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

HRID 270123

반응식

HRID 270123 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-004c7494ad88477b9d69d45ca9932e4a
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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