Lithium Hydroxide → 3-Cyclopentyl-2-(3-fluoro-4-trifluoromethyl-phenyl)-propionic acid

HRID 430241ノート

反応式

HRID 430241 の反応式
C[O:2][C:3](=[O:22])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[C:13]([F:21])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[C:13]([F:21])[CH:12]=2)[C:3]([OH:22])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 537268193-Cyclopentyl-2-(3-fluoro-4-trifluoromethyl-phenyl)-propionic acid methyl ester

生成物 1

HCID 223151913-Cyclopentyl-2-(3-fluoro-4-trifluoromethyl-phenyl)-propionic acid収率 64.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

A solution of 3-cyclopentyl-2-(3-fluoro-4-trifluoromethyl-phenyl)-propionic acid methyl ester (1.80 g, 5.69 mmol) in tetrahydrofuran (15 mL) was treated with a 0.8M aqueous lithium hydroxide solution (7.1 mL, 5.69 mmol). The reaction mixture was stirred at 25° C. for 15 h. The reaction mixture was concentrated in vacuo. The resulting residue was diluted with ethyl acetate (100 mL) and then washed with a 5% aqueous hydrochloric acid solution and a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 2/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(3-fluoro-4-trifluoromethyl-phenyl)-propionic acid (1.11 g, 64%) as a white solid: mp 93-95° C.; FAB-HRMS m/e calcd for C15H16F4O2 (M+H)+ 305.1165, found 305.1175.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe resulting residue was diluted with ethyl acetate (100 mL)
  3. washwashed with a 5% aqueous hydrochloric acid solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d10014092efd480e921065cd7888f779
出典データセット
uspto-grants-2001_11
特許番号
US06320050B1

反応ノート

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