1-Octanethiol → Ethyl 3-(2,6-difluoro-4-hydroxyphenyl)propanoate

HRID 2110844ノート

反応式

HRID 2110844 の反応式
[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[C:4]([F:10])[C:3]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl-].[Al+3].[Cl-].[Cl-].C(S)CCCCCCC>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([F:10])[C:3]=1[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

参加物

5

反応物 3

HCID 81441-OctanethiolHCID 6451240Aluminum(III) ChlorideHCID 23082987Ethyl 3-(2,6-difluoro-4-methoxyphenyl)propanoate

生成物 1

HCID 23082713Ethyl 3-(2,6-difluoro-4-hydroxyphenyl)propanoate収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of ethyl 3-(2,6-difluoro-4-methoxyphenyl)propanoate (1.17 g, 4.79 mmol), aluminum chloride (1.9 g, 14.2 mmol) and 1-octanethiol (1.7 mL, 9.80 mmol) in dichloromethane (20 mL) was stirred for 4 hr while raising the temperature from under ice-cooling to room temperature. The reaction mixture was poured into ice water, and the mixture was stirred for 1 hr. The mixture was extracted with dichloromethane. The extract washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:10-1:5) to give the title compound (1.0 g, yield 91%) as a colorless oil. MS: m/z 231 (MH+).

後処理

  1. temperaturewhile raising the temperature from under ice-
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe extract washed with aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-eda0074ee88a4a35a5b611594fe9a6fc
出典データセット
uspto-grants-2009_04
特許番号
US07517910B2

反応ノート

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