Methyl Thioglycolate → methyl 6-benzyl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate

HRID 505824Notes

Reaction equation

[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]([CH:19]=O)=[C:9]1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][CH3:27])(=[O:25])[CH2:23][SH:24].CC(C)([O-])C.[K+]>C1COCC1>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]2[CH:19]=[C:23]([C:22]([O:26][CH3:27])=[O:25])[S:24][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution (1.1 M) of 1-benzyl-2-chloro-5-phenyl-1H-pyrrole-3-carbaldehyde in THF at 0° C. was treated with methyl thioglycolate (1.5 eq.) and a solution (2 M) of potassium tert-butoxide (2.5 eq.) in THF. The mixture was stirred at 0° C. for 2 h then at RT for 40 h. The reaction was quenched with water and pH was turned to neutral value by addition of aqueous ammonium chloride (saturated solution). The mixture was extracted with AcOEt and the combined organic phase was washed with brine and dried. Evaporation of the solvent gave a residue that was purified by flash chromatography on silica gel (1:30 acetone/toluene) to afford the title compound (38%) as a solid.

Workup

waitat RT for 40 h
customThe reaction was quenched with water and pH
additionwas turned to neutral value by addition of aqueous ammonium chloride (saturated solution)
extractionThe mixture was extracted with AcOEt
washthe combined organic phase was washed with brine
customdried
customEvaporation of the solvent
customgave a residue that
customwas purified by flash chromatography on silica gel (1:30 acetone/toluene)

Sources & evidence

ORD record: ord-dceaec4639154039b363ea0e4b093a20
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781431B2

Reaction notes

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