Lithium Hydroxide → 2-(4-Chloro-3-nitro-phenyl)-3-cyclopentyl-propionic acid

HRID 430212ノート

反応式

HRID 430212 の反応式
C[O:2][C:3](=[O:21])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[C:3]([OH:21])=[O:2])=[CH:12][C:13]=1[N+:18]([O-:20])=[O:19]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 120695062-(4-Chloro-3-nitrophenyl)-3-cyclopentyl-propionic acid methyl ester

生成物 1

HCID 223152892-(4-Chloro-3-nitro-phenyl)-3-cyclopentyl-propionic acid収率 98%

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 2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionic acid methyl ester (260 mg, 0.834 mmol) in tetrahydrofuran (3 mL) was treated with a 0.8M aqueous lithium hydroxide solution (1.25 mL, 1.00 mmol). The reaction mixture was stirred at 25° C. for 15 h. The resulting reaction mixture was partitioned between water (50 mL) and ethyl acetate (50 mL) and then treated with a 1N aqueous hydrochloric acid solution (10 mL). The layers were shaken and separated. The aqueous layer was further extracted with ethyl acetate (50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 2-(4-chloro-3-nitro-phenyl)-3-cyclopentyl-propionic acid (243 mg, 98%) as a yellow solid which was used without further purification: mp 112-115° C.; FAB-HRMS m/e calcd for C14H16ClNO4 (M+H)+ 298.0847, found 298.0851.

後処理

  1. customThe resulting reaction mixture
  2. customwas partitioned between water (50 mL) and ethyl acetate (50 mL)
  3. additiontreated with a 1N aqueous hydrochloric acid solution (10 mL)
  4. stirringThe layers were shaken
  5. customseparated
  6. extractionThe aqueous layer was further extracted with ethyl acetate (50 mL)
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-737c7e11625441009e6e1ba23157742e
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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