Synthesis of 5-(6-hydroxy-7H-purine-8-ylthio)- 2-(N-hydroxyformamido)pentanoic acid

• Yanmei Zhang,
• Greg Elliot,
• Adrian Saldanha,
• Igor Tsigelny,
• Dennis Carson and
• Wolf Wrasidlo

Beilstein J. Org. Chem. 2010, 6, 742–747, doi:10.3762/bjoc.6.93

• , was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 475.0 mg, 2.48 mmol) followed by DMAP (302.0 mg, 2.48 mmol). After stirring at 0 °C for 30 min, benzyl alcohol (402.0 mg, 3.72 mmol) was added. The reaction mixture was stirred at 0 °C for 1 h, then warmed to room temperature

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

• Magnus Rueping and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2010, 6, No. 6, doi:10.3762/bjoc.6.6

• reaction was found by accident, this was probably the first description of a catalytic FC alkylation utilizing a benzyl alcohol. The first systematic investigations of catalytic FC benzylations were performed independently in 1996 and 1997 by Fukuzawa [3][4] and Shimizu et al. [5]. While the latter used 10

• in high yields (Scheme 4). Other rare-earth trifluormethanesulfonates such as Nd(OTf)3 Yb(OTf)3 and Sm(OTf)3 showed similar reactivities and the reaction was later also performed in the ionic liquids [BMIM][OTf] and [BMIM][PF6] [6]. Next to benzyl alcohol, allyl alcohols, dibenzylethers as well as

• . Furthermore, an efficient intramolecular variant of this procedure starting from biaryl benzyl alcohol 23 led to substituted fluorenes 24 which have shown to be valuable scaffolds for blue light emitting polymers (Scheme 11A) [46]. A similar route to fluorenes and other annulated cycloalkanes 26 was

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

• outlet (Figure 2B). The effective mixing was later supported by the high yields and conversions that were achieved for this biphasic reaction. Preliminary reactions were performed using benzyl alcohol as the test substrate in order to establish the optimal flow conditions (Scheme 3). A solution of benzyl

• to residence time, see Supporting Information File 1. During our optimization studies, it was shown that a total flow rate of 100 µL min−1 (aqueous flow rate 56 µL min−1 and organic flow rate 44 µL min−1, approximately 4.8 min residence time) afforded quantitative conversion of benzyl alcohol to

• flow conditions for the benzyl alcohol oxidation, a number of different substrates were examined to test the generality of the AO-TEMPO packed-bed microreactor. High conversions were achieved when using both aromatic and aliphatic alcohols (Table 1, Entries 1–6). Secondary alcohols, which are known to

Convenient method for preparing benzyl ethers and esters using 2-benzyloxypyridine

• Susana S. Lopez and
• Gregory B. Dudley

Beilstein J. Org. Chem. 2008, 4, No. 44, doi:10.3762/bjoc.4.44

• of benzyl trichloroacetimidate using triflic acid, except that alkylation under neutral conditions is compatible with acid- (and base-) sensitive substrates. Results and Discussion 2-Benzyloxypyridine was prepared in 97% yield by heating a mixture of benzyl alcohol, 2-chloropyridine (1.1 equiv), and

• protocols. Experimental 2-Benzyloxypyridine (2): A mixture of benzyl alcohol (11.7 g, 0.108 mol, 1.0 equiv), 2-chloropyridine (13.5 g, 0.119 mol, 1.1 equiv), KOH (20.0 g, 0.356 mol, 3.3 equiv, ground with a mortar and pestle), and anhydrous toluene (210 mL) was heated at reflux (bath temperature: 130 °C

Synthesis of imidazol- 1-yl-acetic acid hydrochloride: A key intermediate for zoledronic acid

• Santosh Kumar Singh,
• Narendra Manne,
• Purna Chandra Ray and
• Manojit Pal

Beilstein J. Org. Chem. 2008, 4, No. 42, doi:10.3762/bjoc.4.42

• KOH-K2CO3 followed by ester hydrolysis in water at 100 °C [10]. In another process [8] for the preparation of zoledronic acid, a benzyl ester of imidazole-1-yl-acetic acid 4 was prepared by reacting imidazole (1) with benzyl chloroacetate generated in situ from benzyl alcohol and chloroacetyl chloride

Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis

• Roger Hunter,
• Sophie C. M. Rees-Jones and
• Hong Su

Beilstein J. Org. Chem. 2007, 3, No. 38, doi:10.1186/1860-5397-3-38

• can present problems in end-game aspects of total synthesis. Thus it was decided to change methyl to the more deprotection-friendly benzyl group. Synthesis of benzyl pyrrolinone 4e was readily achieved by heating 4a with excess benzyl alcohol at 80°C in an acid-catalysed (p-TsOH) exchange with in

m-Iodosylbenzoic acid – a convenient recyclable reagent for highly efficient aromatic iodinations

• Andreas Kirschning,
• Mekhman S. Yusubov,
• Roza Y. Yusubova,
• Ki-Whan Chi and
• Joo Y. Park

Beilstein J. Org. Chem. 2007, 3, No. 19, doi:10.1186/1860-5397-3-19

• diiodinated benzyl alcohol 8n in good yield. Oxidation of the alcohol group was not observed. Based on related iodine(III)-mediated iodinations of arenas [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] we suggest that the hydrated form of 6 oxidizes

Study of thioglycosylation in ionic liquids

• Jianguo Zhang and
• Arthur Ragauskas

Beilstein J. Org. Chem. 2006, 2, No. 12, doi:10.1186/1860-5397-2-12

• glycosyl donors. Glycosylation of 1 and 2 with various alcohols in [bmim]BF4 with methyl triflate. Glycosidation of 1 and benzyl alcohol in [bmim]BF4 with methyl triflate and water. a-c. The percentage of hydrolyzed methyl trifluoromethanesulfonate in DMSO, CDCl3, and [bmim]BF4. Supporting Information