Cesium carbonate → Methyl-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate

HRID 270100Notes

Reaction equation

HRID 270100 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4]C1C([N+]([O-])=O)=CC=CC=1S([O-])(=O)=O.[OH:18][C:19]1[CH:28]=[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:24][O:23][C:21](=[O:22])[C:20]1[CH:25]=[CH:26][C:27]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)=[CH:28][C:19]=1[O:18][CH2:4][C@@H:2]1[CH2:3][O:1]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 10541338Benzoic acid, 2-hydroxy-4-[(4-methoxyphenyl)methoxy]-, methyl esterHCID 866014842(S)-oxiran-2-ylmethyl3-nitrobenzenesulfonate

Product 1

HCID 71654999Methyl-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoateYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2(S)-oxiran-2-ylmethyl3-nitrobenzenesulfonate (518 mg, 2.0 mmol), methyl 2-hydroxy-4-[(4-methoxybenzyl)oxy]benzoate (576.6 mg, 2.0 mmol) and cesium carbonate (Cs2CO3) (812.5 mg, 2.5 mmol) in dimethylformamide (10 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulphate, Na2SO4, filtered, concentrated in vacuo and the residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum ether) to give the subtitled compound (600 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over sodium sulphate, Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-6ff4eff451c845c28d0e98a9a66c68a3
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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