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

HRID 2110844노트

반응식

HRID 2110844 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-eda0074ee88a4a35a5b611594fe9a6fc
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517910B2

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