Cesium carbonate → Methyl 5-methyl-2-[(2S)-oxiran-2-ylmethoxy]benzoate

HRID 270123

反応式

HRID 270123 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+](C1C=C(S(O[CH2:26][C@@H:27]2[CH2:29][O:28]2)(=O)=O)C=CC=1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:12][C:9]1[CH:10]=[CH:11][C:2]([O:1][CH2:26][C@@H:27]2[CH2:29][O:28]2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 89802Methyl 5-methylsalicylateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

生成物 1

HCID 86601490Methyl 5-methyl-2-[(2S)-oxiran-2-ylmethoxy]benzoate収率 72%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of methyl 2-hydroxy-5-methylbenzoate (0.166 g, 1 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (0.26 g, 1 mmol) and caesium carbonate (0.39 g, 1.2 mmol) in dimethylformamide (5 mL) was stirred at room temperature overnight. The mixture was partitioned between water and ethyl acetate, and the organic phase was washed twice with water and once with brine, and finally concentrated. The crude material was purified by flash chromatoghrphy on silica gel (eluent:ethyl acetate/n-heptane), yielding the titled compound (0.16 g, 72%) as colourless oil.

後処理

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washthe organic phase was washed twice with water and once with brine
  3. concentrationfinally concentrated
  4. customThe crude material was purified by flash chromatoghrphy on silica gel (eluent:ethyl acetate/n-heptane)

出典と根拠

ORDレコード
ord-004c7494ad88477b9d69d45ca9932e4a
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

関連ノート

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