Methanol → 5-Diethoxymethyl-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester

HRID 1952574ノート

反応式

HRID 1952574 の反応式
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]#[C:6][C:7](=O)[C:8]([F:11])([F:10])[F:9])[CH3:2].[C:16]([O:20][CH3:21])(=[O:19])[CH2:17][SH:18].CO.C([O-])([O-])=O.[Cs+].[Cs+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1>[CH3:21][O:20][C:16]([C:17]1[S:18][C:5]([CH:4]([O:13][CH2:14][CH3:15])[O:3][CH2:1][CH3:2])=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9])=[O:19]

参加物

6

反応物 4

HCID 887MethanolHCID 16907Methyl ThioglycolateHCID 109770935,5-Diethoxy-1,1,1-trifluoro-pent-3-yn-2-oneHCID 86671257Cs2CO3 MgSO4

生成物 1

HCID 682265135-Diethoxymethyl-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester収率 63.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 5,5-Diethoxy-1,1,1-trifluoro-pent-3-yn-2-one (2.16 g, 9.64 mmol) in THF (30 ml) was cooled to 0° C. (ice bath). Methyl thioglycolate (0.88 ml, 9.64 mmol) was added in one portion and the mixture was stirred at 0° C. for 1.5 h. Methanol (6 ml) and Cs2CO3/MgSO4 (2 g/4 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 0-30% EtOAc in hexane to afford the desired product (1.90 g, 63% yield).

後処理

  1. stirringThe mixture was stirred at 0° C. for 15 min
  2. waitat rt for 15 h
  3. customThe reaction mixture was quenched
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography with 0-30% EtOAc in hexane

出典と根拠

ORDレコード
ord-d691021b643e4f34b5014cb9c3d6edda
出典データセット
uspto-grants-2013_03
特許番号
US08404859B2

反応ノート

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