Trifluoroacetic acid → HCID 86679662、化合物

HRID 577720ノート

反応式

HRID 577720 の反応式
[CH:1]1(/[CH:4]=[CH:5]/[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.[CH2:18]([N:25]([CH2:31]O)[CH2:26][Si](C)(C)C)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH2:18]([N:25]1[CH2:31][C@@H:4]([CH:1]2[CH2:3][CH2:2]2)[C@H:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 11040780ethyl (2E)-3-cyclopropylacrylate2 回HCID 70869782HCID 70869782、化合物

生成物 1

HCID 86679662HCID 86679662、化合物収率 56%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of ethyl (2E)-3-cyclopropylacrylate (5.3 g, 37.9 mmol) and TFA (0.43 g, 3.79 mmol) in DCM (100 mL) was added dropwise {benzyl[(trimethylsilyl)methyl]amino}methanol (13.5 g, 56.8 mmol) at 0° C. After the addition, the mixture was refluxed overnight. TLC (petroleum ether: EtOAc 10:1) indicated most of ethyl (2E)-3-cyclopropylacrylate was consumed. The reaction mixture was quenched with sat. NaHCO3 (100 mL), brine (100 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether: EtOAc=50:1 to 30:1) to give the title compound (5.8 g, 54% yield) as a yellow oil.

後処理

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed overnight
  3. customwas consumed
  4. customThe reaction mixture was quenched with sat. NaHCO3 (100 mL), brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, petroleum ether: EtOAc=50:1 to 30:1)

出典と根拠

ORDレコード
ord-5b0e6e18759340e187af8d1108b4b065
出典データセット
uspto-grants-2015_05
特許番号
US09040547B2

反応ノート

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