Ethyl Thioglycolate → Ethyl 6-(Trifluoromethyl)-1-benzothiophene-2-carboxylate

HRID 1896541Notes

Reaction equation

C1CCN2C(=NCCC2)CC1.[CH2:12]([O:14][C:15](=[O:18])[CH2:16][SH:17])[CH3:13].F[C:20]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:21]=1[CH:22]=O>C1COCC1.[NH4+].[Cl-].CCOC(C)=O>[F:29][C:28]([F:30])([F:31])[C:26]1[CH:27]=[CH:20][C:21]2[CH:22]=[C:16]([C:15]([O:14][CH2:12][CH3:13])=[O:18])[S:17][C:24]=2[CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene, 5 equiv) in THF (1 M) at 0° C. was added a solution of ethyl-2-mercaptoacetate (1.15 equiv) and the reaction stirred at 0° C. for 20 min. A solution of 2-fluoro4-(trifluoromethyl)benzaldehyde (1 equiv) in THF (2 M) was added and the reaction was stirred for an additional 2 h at 0° C. The reaction was diluted with half-saturated NH4Cl and EtOAc. The organic layer was washed with brine and dried over magnesium sulfate. The volatiles were removed under reduced pressure to obtain the title compound as a viscous oil.

Workup

stirringthe reaction was stirred for an additional 2 h at 0° C
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-79aa5a6be70546e6b26d4129064c56ef
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518964B2

Reaction notes

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