Hydrogen Peroxide → HCID 19347997, compound

HRID 1637192Notes

Reaction equation

[OH:1]O.O.[OH:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)=[C:12]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:11][C:10]=2[CH:28]=1>C(O)(=O)C.C(O)C>[OH:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]([S:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)=[O:1])=[C:12]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:11][C:10]=2[CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Hydrogen peroxide in water (0.52 ml of 30% w/v, 4.6 mmol) was added to a solution of ethyl 6-(hydroxymethyl)-3-[(3-methoxyphenyl)sulfanyl]benzo[b]thiophene-2-carboxylate (Preparation 16, 1.73 g, 4.6 mmol) in a mixture of acetic acid (20 ml) and ethanol (10 ml). The mixture was heated to 100° C. for 60 minutes. The solvents were removed by evaporation under reduced pressure, and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was separated, dried (magnesium sulfate) and concentrated under vacuo, and the residue was flash chromatographed on silica gel using 2% ethanol in dichloromethane as eluant. The title compound was isolated as a foam (1.28 g).

Workup

customThe solvents were removed by evaporation under reduced pressure
customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
customThe organic layer was separated
dry with materialdried (magnesium sulfate)
concentrationconcentrated under vacuo
customchromatographed on silica gel using 2% ethanol in dichloromethane as eluant

Sources & evidence

ORD record: ord-3c9f5dde8c764b0a89f1e1676dfa9a05
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040309

Reaction notes

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