m-Chloroperbenzoic acid → HCID 10969232, compound

HRID 1385291Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[CH2:18][C:6]2=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:19])[CH2:3]1.ClC1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)Cl>[CH3:1][C:2]1([CH3:20])[CH2:18][C:6]2=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[S:8][C:9]([S:10]([CH3:11])=[O:26])=[C:5]2[C:4](=[O:19])[CH2:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

6,6-Dimethyl-3-methylthio-1-(pyrid-2-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (200 mg, 0.66 mmol) was dissolved in CH2Cl2 (20 mL) and cooled to −78° C. Meta-chloroperoxybenzoic acid (82 mg of 70% (w/w); 0.66 mmol) was dissolved in CH2Cl2 (5 mL) and added dropwise to the solution, which was allowed to stir at −50° C. for 1 h, then warmed to room temperature. The mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine. After drying (Na2SO4), the solution was evaporated to dryness and the residue was purified by chromatography on silica gel, eluting with ethyl acetate:hexane (1:1). The title compound was isolated as a white solid (160 mg, 79%). 1HNMR (360 MHz, CDCl3)δ 1.08 (3H, s), 1.11 (3H, s), 2.43 (1H, d, J=18 Hz), 2.53 (1H, d, J=18 Hz), 3.00 (3H, s), 3.03 (2H, s), 7.24-7.28 (1H, m), 7.52-7.54 (1H, m), 7.76-7.80 (1H, m), 8.64-8.66 (1H, m). MS (ES+) 320 (M+1).

Workup

additionadded dropwise to the solution, which
temperaturewarmed to room temperature
washwashed with saturated sodium hydrogen carbonate solution, water and brine
dry with materialAfter drying (Na2SO4)
customthe solution was evaporated to dryness
customthe residue was purified by chromatography on silica gel
washeluting with ethyl acetate:hexane (1:1)

Sources & evidence

ORD record: ord-c54e31be0288490b8368f20ed51c3840
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262103B1

Reaction notes

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