Benzenesulfonyl chloride → HCID 18790109, compound

Participants

Reaction Conditions

Reaction Steps

1-(1-Hydroxy-5-phenylpentyl)cyclopentane carboxylic acid (11.3 g, 40.9 mmol) is dissolved in pyridine (90 mL) and cooled to 0° C. Benzenesulfonyl chloride (10.4 mL, 81 mmol) is added over 1 minute and the reaction is kept at 0° C. overnight. The reaction is poured into ice (100 mL) and the product extracted into ether (2×100 mL). The ether layer is washed with NaHCO3 (100 mL), 1 N HCl (100 mL) and water (2×100 mL). The solution is dried over MgSO4 and the solvent removed in vacuo (without heat). The crude product is purified by column chromatography (silica, 15% ether in petroleum ether) to yield 3-(4-phenylbutyl)-2-oxaspiro[3,4]octan-1-one (5.6 g, 54%): 1H NMR (300 MHz, CDCl3) δ 7.30-7.25 (m, 2H), 7.20-7.15 (m, 3H), 4.31-4.26 (m, 1H), 2.63 (t, J=7.6 Hz, 2H), 2.22-2.13 (m, 1H), 1.99-1.26 (m, 13H).

Provenance & Evidence