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Methyl iodide → (S)-2-Methoxy-3-phenylpropanoic acid

HRID 1482189
ノート
印刷プレビュー

反応式

HRID 1482189 の反応式
[OH:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[H-].[Na+].[CH3:15]I>C1COCC1>[CH3:15][O:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4447183-Phenyllactic acid, (S)-

生成物 1

HCID 11858535(S)-2-Methoxy-3-phenylpropanoic acid収率 65.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

(S)-2-Hydroxy-3-phenylpropanoic acid (1.0 g, 6.02 mmol) was dissolved in THF (100 ml), sodium hydride (0.48 g, 12.00 mmol) and methyl iodide (1.71 g, 12.04 mmol) were added, and the mixture was stirred at 65° C. for one hour. After leaving to cool, the reaction solution was concentrated under reduced pressure and adjusted to pH 4 by adding a 6 M aqueous hydrochloric acid solution thereto. The aqueous layer was extracted with ethyl acetate, the organic layer was concentrated, and the resulting residue was purified by column chromatography (dichloromethane:methanol=10:1) to afford the title compound (0.71 g, 59%).

後処理

  1. customAfter leaving
  2. temperatureto cool
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. additionby adding a 6 M aqueous hydrochloric acid solution
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. concentrationthe organic layer was concentrated
  7. customthe resulting residue was purified by column chromatography (dichloromethane:methanol=10:1)

出典と根拠

ORDレコード
ord-0b055f01eeec4ece90aa1dbb1d8ffac2
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409952B2

反応ノート

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