Hydrogen Peroxide → HCID 19348001, compound

HRID 1637202Notes

Reaction equation

[OH:1]O.O.[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:19]([S:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[S:17][C:16]=2[CH:32]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)(=O)C.O1CCCC1>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:19]([S:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:1])=[C:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[S:17][C:16]=2[CH:32]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Hydrogen peroxide in water (0.15 ml of 30% w/v, 1.3 mmol) was added to a solution of ethyl 6-(benzyloxy)-3-(phenylsulfanyl)benzo[b]thiophene-2-carboxylate (Example 17--500 mg, 1.2 mmol) in acetic acid (5 ml) and tetrahydrofuran (5 ml). The mixture was heated to 100° C. for 3 hours. The solvents were removed by evaporation under reduced pressure, and the residue was partitioned between diethyl ether and aqueous sodium bicarbonate solution. The organic layer was separated, dried (magnesium sulfate) and concentrated under vacuo, and the residue was crystallised from dichloromethane and diisopropyl ether to give the title compound as a colourless solid (455 mg).

Workup

customThe solvents were removed by evaporation under reduced pressure
customthe residue was partitioned between diethyl ether and aqueous sodium bicarbonate solution
customThe organic layer was separated
dry with materialdried (magnesium sulfate)
concentrationconcentrated under vacuo
customthe residue was crystallised from dichloromethane and diisopropyl ether

Sources & evidence

ORD record: ord-896c14dfa2fc4ad9ba2aa32b6fdacdcd
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040309

Reaction notes

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