Potassium Hydroxide → Rac-cyclohexyloxy-(3,4-dichloro-phenyl)-acetic acid

HRID 1019199ノート

反応式

HRID 1019199 の反応式
C[O:2][C:3](=[O:20])[CH:4]([O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1.[OH-].[K+]>C(O)C.O>[CH:14]1([O:13][CH:4]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=2)[C:3]([OH:20])=[O:2])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 67484331Rac-cyclohexyloxy-(3,4-dichloro-phenyl)-acetic acid methyl ester

生成物 1

HCID 12044175Rac-cyclohexyloxy-(3,4-dichloro-phenyl)-acetic acid収率 97%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
25 °C

実験手順

A solution of rac-cyclohexyloxy-(3,4-dichloro-phenyl)-acetic acid methyl ester (527 mg, 1.66 mmol) in ethanol (15 mL) was treated with a solution of potassium hydroxide (233 mg, 4.15 mmol) in water (2 mL) and the mixture was stirred at 25° C. After 3 h, the reaction was diluted with water (5 mL), and the ethanol was removed in vacuo. The aqueous layer was then acidified to pH 2 with 1N hydrochloric acid and extracted with dichloromethane (3×15 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residual oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 chloroform/methanol plus 1% acetic acid) to give rac-cyclohexyloxy-(3,4-dichloro-phenyl)-acetic acid (487 mg, 97% yield) as a colorless oil: EI-HRMS m/e calcd for C14H16Cl2O3 (M+) 302.0477, found 302.0486.

後処理

  1. customthe ethanol was removed in vacuo
  2. extractionextracted with dichloromethane (3×15 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residual oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 chloroform/methanol plus 1% acetic acid)

出典と根拠

ORDレコード
ord-06cda332301340d7a953af2226e90b1e
出典データセット
uspto-grants-2002_11
特許番号
US06486184B2

反応ノート

読み込み中…