m-Chloroperbenzoic acid → HCID 12714621, compound

HRID 1683348Notes

Reaction equation

[C:1]1([S:7][C:8](=[CH2:11])[CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl>[C:1]1([S:7]([C:8](=[CH2:11])[CH2:9][OH:10])=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 0.91 g (5.5 mmol) of 2-(phenylthio)-2-propenyl alcohol in 60 mL of CH2Cl2 at -78° C. was added 1.11 g (5.5 mmol) of 85% m-chloroperbenzoic acid. The reaction mixture was stirred for 1 hour at -78° C. The cooling bath was removed and the mixture allowed to warm to room temperature. The mixture was filtered, and then extracted with three 50-mL portions of saturated NaHCO3. The organic layer was dried over MgSO4, filtered, and the solvent removed in vacuo from a water bath at 45° C. The residue was flash chromatographed on silica gel (230-400 mesh, 4×12-cm packed column) with 80% EtOAc/Skelly B as eluant, to give 0.57 g (57%) of the sulfoxide as a colorless oil; IR (neat) cm1 3360, 1440, 1030, 990, 930, 750, 690; 1H NMR (CDCl3) δ4.00 (s, 1H, allylic), 4.15 (s, 1H, allylic), 4.40 (bs, 1H, OH), 5.90 (t, J=1 Hz, 1H, vinyl), 6.05 (s, 1H, vinyl), 7.35-7.80 (m, 5H, phenyl).

Workup

customThe cooling bath was removed
temperatureto warm to room temperature
filtrationThe mixture was filtered
extractionextracted with three 50-mL portions of saturated NaHCO3
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customthe solvent removed in vacuo from a water bath at 45° C
customchromatographed on silica gel (230-400 mesh, 4×12-cm packed column) with 80% EtOAc/Skelly B as eluant

Sources & evidence

ORD record: ord-3ae9468575864ac0a2d1c70d1269fcff
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05637719

Reaction notes

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