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Search for "sodium hydride" in Full Text gives 132 result(s) in Beilstein Journal of Organic Chemistry.

Self-association of an indole based guanidinium-carboxylate-zwitterion: formation of stable dimers in solution and the solid state

  • Carolin Rether,
  • Wilhelm Sicking,
  • Roland Boese and
  • Carsten Schmuck

Beilstein J. Org. Chem. 2010, 6, No. 3, doi:10.3762/bjoc.6.3

Graphical Abstract
  • -indole-2-carboxylate 3 was reduced by reaction with hydrogen in the presence of Pd/C to provide the amine 4 in a yield of 98%. For the next stept, first, thiourea was N-Boc-protected at both amino-functions following a literature procedure [20]. Thiourea was deprotonated with sodium hydride and
  • (w), 2939 (w), 1668 (s), 1250 (s), 1215(s) cm−1; HR-MS (ESI) calcd for [M+H]+: 205.0972; found 205.0979. N,N’-Di-(tert-butoxycarbonyl)thiourea (5): To a stirred solution of thiourea (570 mg, 7.50 mmol) in dry tetrahydrofuran (150 mL) sodium hydride (1.35 g, 33.80 mmol, 60% in mineral oil) was added
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Published 14 Jan 2010

Mitomycins syntheses: a recent update

  • Jean-Christophe Andrez

Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33

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  • selectively mesylated on hydroxyl 2. Treatment with sodium hydride formed the epoxide. The acetate was removed and the epoxide was opened with lithium azide at 150°C. The two resulting alcohols were mesylated and the primary mesylate displaced with benzylamine. The resulting secondary amine was benzylated to
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Published 08 Jul 2009

A biphasic oxidation of alcohols to aldehydes and ketones using a simplified packed- bed microreactor

  • Andrew Bogdan and
  • D. Tyler McQuade

Beilstein J. Org. Chem. 2009, 5, No. 17, doi:10.3762/bjoc.5.17

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  • catalysts functionalized with an acetylene moiety can be tethered to AO using a Huisgen cycloaddition [39]. Azide-functionalized AO resin (AO-N3, 2) was prepared by treating AO with sodium azide (Scheme 1) [41]. The coupling of 4-hydroxy-TEMPO 3 with propargyl bromide (4) using sodium hydride yielded the
  • (2 × 50 mL), Et2O (1 × 25 mL), and dried under vacuum. Elemental analysis afforded a loading of 1.0 mmol N3/g resin. Propargyl ether TEMPO 5 Sodium hydride (150 mg, 6.3 mmol, 1.1 equiv) was added to DMF (10 mL) and stirred at RT. 4-hydroxy-TEMPO (1.02 g, 5.9 mmol, 1.0 equiv) in DMF (10 mL) was added
  • drop wise to the sodium hydride suspension at 0 °C and stirred until gas evolution ceased. Propargyl bromide (80% in toluene, 800 μL, 7.4 mmol, 1.3 equiv) in DMF (10 mL) was added at 0 °C and the reaction was allowed to warm up to RT and stirred overnight. The reaction was quenched with water and the
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Published 29 Apr 2009

End game strategies towards the total synthesis of vibsanin E, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A

  • Brett D. Schwartz,
  • Craig M. Williams and
  • Paul V. Bernhardt

Beilstein J. Org. Chem. 2008, 4, No. 34, doi:10.3762/bjoc.4.34

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  • epoxide ring opened product (i.e. 28) was isolated (via epoxide 29). Subsequent treatment of the crude material (i.e. 28) with sodium hydride gave as the sole product the TBS protected α-hydroxy ketone 30 in 80% yield over two steps, via a 1,2-Brook rearrangement. The unprotected derivative 31 could be
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Published 08 Oct 2008

Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(−)-8-methyl- 5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(−)-4-pentyloctahydro- 2H-quinolizin- 1-yl]methanol

  • Joseph P. Michael,
  • Claudia Accone,
  • Charles B. de Koning and
  • Christiaan W. van der Westhuyzen

Beilstein J. Org. Chem. 2008, 4, No. 5, doi:10.1186/1860-5397-4-5

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  • lactam (+)-26 was troublesome, giving at best a yield of 52% when performed with sodium hydride and tetrabutylammonium iodide in N,N-dimethylformamide. An effortless thionation of 26 with Lawesson's reagent in boiling toluene produced the thiolactam (+)-27 in 92% yield. Eschenmoser sulfide contraction
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Published 18 Jan 2008

Aroylketene dithioacetal chemistry: facile synthesis of 4-aroyl- 3-methylsulfanyl- 2-tosylpyrroles from aroylketene dithioacetals and TosMIC

  • H. Surya Prakash Rao and
  • S. Sivakumar

Beilstein J. Org. Chem. 2007, 3, No. 31, doi:10.1186/1860-5397-3-31

Graphical Abstract
  • H. Surya Prakash Rao S. Sivakumar Department of Chemistry, Pondicherry University, Puducherry, 605 014, India 10.1186/1860-5397-3-31 Abstract The cycloaddition of the von Leusen's reagent (p-tolylsulfonyl)methyl isocyanide (TosMIC) to α-aroylketene dithioacetals (AKDTAs) in the presence of sodium
  • hydride in THF at rt resulted in a facile synthesis of the 4-aroyl-3-methylsulfanyl-2-tosylpyrroles 3 in good yield along with a minor amount of 4-[(4-methylphenyl)sulfonyl]-1-[(methylsulfanyl)methyl]-1H-imidazole 4. This study lead to the synthesis of 2,3,4-trisubstiuted pyrroles having 1-naphthoyl/2
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Published 28 Sep 2007

Total syntheses of oxygenated brazanquinones via regioselective homologous anionic Fries rearrangement of benzylic O-carbamates

  • Glaucia Barbosa Candido Alves Slana,
  • Mariângela Soares de Azevedo,
  • Rosângela Sabattini Capella Lopes,
  • Cláudio Cerqueira Lopes and
  • Jari Nobrega Cardoso

Beilstein J. Org. Chem. 2006, 2, No. 1, doi:10.1186/1860-5397-2-1

Graphical Abstract
  • -diethylcarbamoyl chloride, and sodium hydride afforded the carbamates 2a-2d (Scheme 2). The carbamates 2a-2c were cyclized in the presence of excess sec-BuLi in THF at -78°C to afford the desired brazanquinones 1a-1c in reasonable yields (54%–57%) (Scheme 2). The mechanism suggested by us and shown in Scheme 1
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Published 21 Feb 2006
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