1-Octanethiol → Benzenepropanoic acid, alpha,alpha-difluoro-4-hydroxy-, ethyl ester

HRID 732194노트

반응식

HRID 732194 반응식
[F:1][C:2]([F:17])([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].C(S)CCCCCCC>ClCCl>[F:1][C:2]([F:17])([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

참가 물질

5

반응물 3

HCID 81441-OctanethiolHCID 6451240Aluminum(III) ChlorideHCID 15487039Ethyl 2,2-difluoro-3-(4-methoxyphenyl)propanoate

생성물 1

HCID 22345522Benzenepropanoic acid, alpha,alpha-difluoro-4-hydroxy-, ethyl ester수율 56%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of ethyl 2,2-difluoro-3-(4-methoxyphenyl)propanoate (1.72 g, 7.05 mmol) synthesized according to the method described in Synthesis, vol. 13, pages 1917-1924, 2000 and aluminum chloride (2.82 g, 21.2 mmol) in dichloromethane (50 mL) was added dropwise 1-octanethiol (2.06 g, 14.1 mmol) and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was poured into ice water and stirred for 30 min. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=8:92-60:40) to give the title compound (0.90 g, yield 56%) as a colorless oil.

후처리

  1. stirringstirred for 30 min
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=8:92-60:40)

출처 및 근거

ORD 기록
ord-b56224febd794d358837ce9b06f9d967
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585880B2

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