Cesium carbonate → tert-butyl 2-[(2S)-oxiran-2-ylmethoxy]benzoate

HRID 270120Notes

Reaction equation

HRID 270120 reaction equation
[C:1]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[N+](C1C=C(S(O[CH2:28][C@@H:29]2[CH2:31][O:30]2)(=O)=O)C=CC=1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[O:30]1[CH2:31][C@H:29]1[CH2:28][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 11424104Tert-butyl 2-hydroxybenzoate

Product 1

HCID 86601489tert-butyl 2-[(2S)-oxiran-2-ylmethoxy]benzoateYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl salicylate (2.01 g, 10.3 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (2.69 g, 10.4 mmol) and cesium carbonate (4.05 g, 12.4 mmol) in dimethylformamide (20 mL) was stirred at room temperture overnight. The reaction mixture was partitioned between ethyl acetetate and water. The organic layer was dried over sodium sulphate, Na2SO4, filtered, concentrated in vacuo. The residue was purified by silica gel flash chromatography (ethyl acetate 40%, heptane 60%) and gave the subtitle compound (2.3 g, 89%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetetate 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 (ethyl acetate 40%, heptane 60%)

Sources & evidence

ORD record
ord-e20bad53797a4c1897d8b53beddce91d
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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