Benzenesulfonyl chloride → HCID 18790109, compound

HRID 1107155Notes

Reaction equation

O[CH:2]([C:13]1([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(S(Cl)(=O)=O)C=CC=CC=1>N1C=CC=CC=1>[C:7]1([CH2:6][CH2:5][CH2:4][CH2:3][CH:2]2[C:13]3([CH2:14][CH2:15][CH2:16][CH2:17]3)[C:18](=[O:19])[O:20]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

extractionthe product extracted into ether (2×100 mL)
washThe ether layer is washed with NaHCO3 (100 mL), 1 N HCl (100 mL) and water (2×100 mL)
dry with materialThe solution is dried over MgSO4
customthe solvent removed in vacuo (without heat)
customThe crude product is purified by column chromatography (silica, 15% ether in petroleum ether)

Sources & evidence

ORD record: ord-e3bf10ff92654ec690d0236367bf974f
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057369

Reaction notes

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