Lithium Hydroxide → 3-Cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid

HRID 1936233ノート

反応式

HRID 1936233 の反応式
C[O:2][C:3](=[O:22])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][CH2:19][O:20][CH3:21])=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1.O>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[C:18][CH2:19][O:20][CH3:21])=[CH:13][CH:12]=2)[C:3]([OH:22])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 674837663-Cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid methyl ester

生成物 1

HCID 224652903-Cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid収率 97%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

A solution of 3-cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid methyl ester (485 mg, 1.61 mmol) in tetrahydrofuran (10 mL) and water (10 mL) was treated with lithium hydroxide (775 mg, 18.5 mmol). The reaction mixture was stirred at 25° C. for 48 h. At this time, the reaction was concentrated in vacuo. The residue was re-dissolved in water (40 mL) which was then acidified to pH=2 with concentrated hydrochloric acid. This solution was extracted with ethyl acetate (2×40 mL). The aqueous layers were back extracted with ethyl acetate (1×40 mL). The combined organic extracts were then washed with a half-saturated aqueous sodium chloride solution (1×40 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid (447 mg, 96.7%) as a white solid: mp 82-85° C.; EI-HRMS m/e calcd for C18H22O3 (M+) 286.1568, found 286.1563.

後処理

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. dissolutionThe residue was re-dissolved in water (40 mL) which
  3. extractionThis solution was extracted with ethyl acetate (2×40 mL)
  4. extractionThe aqueous layers were back extracted with ethyl acetate (1×40 mL)
  5. washThe combined organic extracts were then washed with a half-saturated aqueous sodium chloride solution (1×40 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-63bfed06608e4a2babac3a9a86fc232d
出典データセット
uspto-grants-2002_05
特許番号
US06388071B2

反応ノート

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