Ethanethiol → Ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate

HRID 1741815Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of ethyl 4-[1-(4-methoxybenzoyl)-indolizin-3-yl]butyrate (640 mg) and ethanethiol (2.5 ml) in dichloromethane (8 ml) was added aluminum chloride (700 mg) at 0° C. After stirred at 0° C. for 10 minutes, the solvent was evaporated and the residue was poured into a mixture of ethyl acetate and ice-water. The organic layer was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel column eluting with a mixture of chloroform and ethyl acetate (4:1) to give ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate (344 mg) as yellow solid.

Workup

customthe solvent was evaporated
additionthe residue was poured into a mixture of ethyl acetate and ice-water
customThe organic layer was separated
washwashed with aqueous sodium bicarbonate and brine
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was chromatographed on silica gel column
washeluting with a mixture of chloroform and ethyl acetate (4:1)

Sources & evidence

ORD record: ord-4eb4a9310a6f40f6ae9400f4148f966c
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334716

Reaction notes

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