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

HRID 732194ノート

反応式

HRID 732194 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b56224febd794d358837ce9b06f9d967
出典データセット
uspto-grants-2009_09
特許番号
US07585880B2

反応ノート

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