m-Chloroperbenzoic acid → (+/-)-2-(Benzyloxymethyl)-3-(2-chlorophenyl)oxirane

HRID 1506985Notes

Reaction equation

HRID 1506985 reaction equation
[CH2:1]([O:8][CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:24]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH:10]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[O:24]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 90033540(E)-1-(3(benzyloxy)prop-1enyl)2-chlorobenzene

Product 1

HCID 90017867(+/-)-2-(Benzyloxymethyl)-3-(2-chlorophenyl)oxiraneYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-1-(3-(benzyloxy)prop-1-enyl)-2-chlorobenzene(Preparation example 367, 4.94 g, 22 mmole) in CH2Cl2 (110 mL) was added 3-chloroperoxybenzoic acid (70˜75%, 8 g, 33 mmole) portionwise at 0° C. The mixture was stirred for 18 hr at room temperature. The TLC showed complete consumption of SM. The reaction mixture was quenched with H2O at 0° C. then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with sat′ NaHCO3, H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (4.3 g, 60˜80%).

Workup

  1. customconsumption of SM
  2. customThe reaction mixture was quenched with H2O at 0° C.
  3. extractionthen extracted with EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. customseparated
  6. washThe combined organic layer was washed
  7. dry with materialdried over MgSO4
  8. customevaporated under reduced pressure
  9. customThe crude compound was purified by silica ge column

Sources & evidence

ORD record
ord-800707e93af84eb7a01aca1bb8412dd9
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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