Methanesulfonyl chloride → Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester

HRID 77025ノート

反応式

HRID 77025 の反応式
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([OH:16])[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:2].CCN(C(C)C)C(C)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([O:16][S:28]([CH3:27])(=[O:30])=[O:29])[C:6]1[CH:7]=[CH:8][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:10][CH:11]=1)[CH3:2]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 20286794Hydroxy 4-(trifluoromethyl)phenylacetic acid ethyl ester

生成物 1

HCID 59401272Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester収率 100.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Hydroxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester (I101) (440 mg, 1.77 mmol) and DIPEA (0.43 mL, 2.48 mmol) are dissolved in dry DCM (17 mL) and cooled at 0° C. under N2. Methansulfonyl chloride (0.18 mL, 2.30 mmol) is added dropwise to the solution and the resulting mixture is allowed to warm to RT and stirred for 3 hours. The mixture is diluted with DCM and washed with sat. NaHCO3, water and brine. The organic layer is dried (Na2SO4), filtered and evaporated to obtain intermediate I150 as a yellow oil (578 mg, quantitative yield), which is used in the next step without any further purification.

後処理

  1. temperatureto warm to RT
  2. washwashed with sat. NaHCO3, water and brine
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-5f253bf3286f40bab843f3e034b780fd
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

反応ノート

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