Methanol → 5-Diethoxymethyl-3-phenyl-thiophene-2-carboxylic acid methyl ester
Reaction equation
[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[C:5]#[C:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O)[CH3:2].[C:18]([O:22][CH3:23])(=[O:21])[CH2:19][SH:20].CO.C([O-])([O-])=O.[Cs+].[Cs+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1>[CH3:23][O:22][C:18]([C:19]1[S:20][C:5]([CH:4]([O:15][CH2:16][CH3:17])[O:3][CH2:1][CH3:2])=[CH:6][C:7]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:21]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4,4-Diethoxy-1-phenyl-but-2-yn-1-one (5.7 g, 24.54 mmol) in THF (75 ml) was cooled to 0° C. (ice bath). Methyl thioglycolate (2.2 ml, 24.54 mmol) was added in one portion and the mixture was stirred at 0° C. for 2 h. Methanol (25 ml) and Cs2CO3/MgSO4 (8 g/16 g, pre-dried at 200° C. in vacuum) were added at 0° C. The mixture was stirred at 0° C. for 15 min and then at rt for 15 h. The reaction mixture was quenched by pouting into EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 0-40% EtOAc in hexane to afford the desired product (5.07 g, 64% yield).
Workup
- stirringThe mixture was stirred at 0° C. for 15 min
- waitat rt for 15 h
- customThe reaction mixture was quenched
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography with 0-40% EtOAc in hexane
Sources & evidence
- ORD record
- ord-c9b7d79c1fc349e490072d5770b0dc68
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404859B2
Reaction notes
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