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

HRID 270106Notes

Reaction equation

HRID 270106 reaction equation
[N+](C1C=C(S(O[CH2:14][C@@H:15]2[CH2:17][O:16]2)(=O)=O)C=CC=1)([O-])=O.[OH:18][C:19]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:29][C:27]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([O:18][CH2:14][C@@H:15]2[CH2:17][O:16]2)[CH:28]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl esterHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 71655300Methyl 4-methyl-2-[(2S)-oxiran-2-ylmethoxy]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (777.7 mg, 3.0 mmol), methyl 2-hydroxy-4-methylbenzoate ((498.5 mg, 3.0 mmol) and Cs2CO3 (1.17 g, 3.6 mmol) in DMF (10 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-20% ethyl acetate in petroleum spirit) to give the subtitled compound (500 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (0-20% ethyl acetate in petroleum spirit)

Sources & evidence

ORD record
ord-5da029fadcd84547a917c3e533b8f518
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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