Benzyl Alcohol → HCID 131715643, compound

Participants

Reaction Steps

Boc-diacid (F) (1.34 g, 3.75 mmol) in methylene chloride (30 ml) was treated with benzyl alcohol (1.94 ml, 18.75 mmol), dimethylaminopyridine (1.01 g, 8.25 mmol) and N,N'-dicyclohexylcarbodiimide (1.70 g, 8.25 mmol) at room temperature and the mixture was stirred at room temperature for 72 hours. The reaction mixture was then filtered, evaporated at reduced pressure and the residue was dissolved in ethyl acetate which was washed with 3N hydrochloric acid, dried over MgSO4 and evaporated at reduced pressure. Purification of the residue by flash chromatography (silica gel, 15% ethyl acetate/hexane) gave 1.27 g (63%) of (I): 1HNMR (CDCl3): 7.35 (S, 10H), 5.15 (d,J=2.4 Hz, 2H), 5.07 (S, 2H) 5.05-4.70 (m, 1H), 4.50-4.05 (m, 1H), 2.27 (S, 2H), 1.45 (S, 9H) and 2.00-03 (m, 16H).

Provenance & Evidence