Water → HCID 15463517, compound

HRID 430791Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][S:9][CH2:10][CH2:11][C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:15]=3[O:14][C:13]=2[CH3:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N(Br)C(=[O:31])C1.O>CO>[C:1]1([CH2:7][CH2:8][S:9]([CH2:10][CH2:11][C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:15]=3[O:14][C:13]=2[CH3:27])=[O:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Methyl (3-(2-(2-phenylethylthio)ethyl)-2-methylbenzofuran-7-yloxy)acetate (340 mg) was dissolved in methanol (15 ml) and the obtained solution was cooled to −10° C. To this solution, NBS (190 mg) was added for 5 minutes and the resulting mixture was stirred at −10° C. for 30 minutes. This reaction solution was poured into water layer (100 ml) and the resultant was extracted twice with ethyl acetate (30 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: dichloromethane/ethyl acetate=2/1) using silica gel to obtain the desired compound (225 mg, yield: 64%).

Workup

extractionthe resultant was extracted twice with ethyl acetate (30 ml)
washwashed with saturated brine
dry with materialby drying over sodium sulfate
customAfter removing the sodium sulfate
filtrationby filtration
customthe solvent was removed under reduced pressure
customthe residue was purified by column chromatography (solvent: dichloromethane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-2a757e1723a94756beb2045cd6f98a7b
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06323235B1

Reaction notes

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