Formic Acid → Ethyl 3-(2,4,6-trifluorophenyl)propanoate

HRID 705821

反応式

HRID 705821 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(O)=O>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

5

反応物 2

HCID 284Formic AcidHCID 574127793-(2,4,6-Trifluoro-phenyl)-acrylic acid ethyl ester

生成物 1

HCID 53425006Ethyl 3-(2,4,6-trifluorophenyl)propanoate収率 89.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

Pd/C (0.5 g, 10%, 50% water wet) was added to a solution of ethyl (2E)-3-(2,4,6-trifluorophenyl)-2-propenoate (2.0 g, 8.69 mmol) in ethyl acetate (40 mL) under an argon atmosphere, followed by TEA (2.409 mL, 17.38 mmol) and formic acid (1.666 mL, 43.4 mmol). The reaction mixture was refluxed at 90° C. under argon for 1 h. The reaction mixture was filtered through a celite pad and the filtrate was then washed with water, 5% NaHCO3 solution and brine, before being dried over Na2SO4. Solvent evaporation under reduced pressure yielded the title compound as a pale yellow oil (1.8 g, 89% yield). LCMS: 3.41 min, [M+H+]=232.9

後処理

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washthe filtrate was then washed with water, 5% NaHCO3 solution and brine
  3. dry with materialbefore being dried over Na2SO4
  4. customSolvent evaporation under reduced pressure

出典と根拠

ORDレコード
ord-6d7f6fd76ca64d2bbbae274533215244
出典データセット
uspto-grants-2015_11
特許番号
US09174968B2

関連ノート

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