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

HRID 270123

Reaction equation

HRID 270123 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-004c7494ad88477b9d69d45ca9932e4a
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Linked notes

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