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

HRID 732185ノート

反応式

HRID 732185 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 from under ice-cooling to room temperature for 4 hr. The reaction mixture was poured into ice water, and the mixture was stirred for 1 hr. The mixed solution was extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=1:10-1:5) to give the title compound (1.0 g, yield 91%) as a colorless oil.

後処理

  1. extractionThe mixed solution was extracted with dichloromethane
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=1:10-1:5)

出典と根拠

ORDレコード
ord-e03c5e2822144bcbbc135f74c9e90a20
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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