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

HRID 2365971Notes

Reaction equation

HRID 2365971 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-feb499f4b5ea44578065c8e90fa79ed5
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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