m-Chloroperbenzoic acid → Acetic acid 4-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester

HRID 453764Notes

Reaction equation

HRID 453764 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](C(=O)C)=[C:11]([O:18][CH2:19][C@H:20]2[CH2:22][O:21]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=[C:26]([C:30]([O:32]O)=[O:31])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:32][C:30](=[O:31])[CH3:26])=[C:11]([O:18][CH2:19][C@H:20]2[CH2:22][O:21]2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 866447131-[4-Benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl]ethanone

Product 1

HCID 86644714Acetic acid 4-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-[4-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl]ethanone (1.62 g, 5.43 mmol) in DCM (60 ml) was added m-chloroperbenzoic acid (2.15 g) and solid NaHCO3 (3.24 g). Stirring was continued at 40° C. for 1 h. The mixture was filtered and the filtrate was washed once with 10% NaHSO4 solution and then twice with NaHCO3 solution. The organic layer was washed with water and brine, dried with Na2SO4. The solvent was removed under reduced pressure. The crude product obtained (1.34 g) was sufficiently pure for the next step.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed once with 10% NaHSO4 solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-de294357580f45a882c96490f7776423
Source dataset
uspto-grants-2013_07
Patent number
US08492549B2

Reaction notes

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