Cesium carbonate → 6-Methoxy-2-methyl-1,3-benzoxazolyl (2s)oxiranylmethyl ether

HRID 132594Notes

Reaction equation

HRID 132594 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]2=[C:11]([OH:13])[CH:12]=1.[N+](C1C=C(C=CC=1)O[CH2:21][C@@H:22]1[CH2:24][O:23]1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[O:23]1[CH2:24][C@H:22]1[CH2:21][O:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=12

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 7036817(S)-2-((3-Nitrophenoxy)methyl)oxiraneHCID 691989936-Methoxy-2-methyl-1,3-benzoxazol-4-ol

Product 1

HCID 867606936-Methoxy-2-methyl-1,3-benzoxazolyl (2s)oxiranylmethyl etherYield 83.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-methoxy-2-methyl-1,3-benzoxazol-4-ol (0.11 g, 0.60 mmol), (2S)-2-[(3-nitrophenoxy)methyl]oxirane (0.16 g, 0.79 mmol) and cesium carbonate (0.44 g, 1.37 mmol) in dry DMF (4 mL) was stirred at room temperature for 5 hours. After aqueous work-up the crude product was purified by flash chromatography (SiO2, toluene-ethyl acetate, 3:1) to afford the subtitle compound (0.118 g, 83.7%).

Workup

  1. customAfter aqueous work-up the crude product was purified by flash chromatography (SiO2, toluene-ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-81c9ebb3825946a38f8013b5dc13a5ae
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

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