Sodium Dithionite → (2R,3R)-2,3-Bis((benzyloxy)methyl)oxirane

HRID 1029982Notes

Reaction equation

HRID 1029982 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[CH:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:29])C=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>ClCCl>[CH2:1]([O:8][CH2:9][CH:10]1[O:29][CH:11]1[CH2:12][O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 70297m-Chloroperbenzoic acidHCID 40541091,4-Bis(benzyloxy)-2-butene

Product 1

HCID 13255030(2R,3R)-2,3-Bis((benzyloxy)methyl)oxiraneYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.0 g (0.022 mol) of 1,4-bis-(benzyloxy)-2-butene in 80 ml of dichloromethane was added 5.4 g (0.022 mol) of m-chloroperbenzoic acid (purity: 70%) in four portions under ice-cooling and stirring. The resulting mixture was stirred at the same temperature for 1 hour. After filtering off the white precipitate thus formed, the filtrate was poured into a 10% aqueous solution of sodium hydrosulfite. The mixture was extracted with dichloromethane, washed with water and dried. After distilling off the solvent, the obtained residue was purified by column chromatography (silica gel, hexane/ether) to thereby give 4.2 g of 1,4-bis(benzyloxy)-2,3-epoxybutane as a colorless liquid.

Workup

  1. temperaturecooling
  2. stirringThe resulting mixture was stirred at the same temperature for 1 hour
  3. filtrationAfter filtering off the white precipitate
  4. customthus formed
  5. extractionThe mixture was extracted with dichloromethane
  6. washwashed with water
  7. customdried
  8. distillationAfter distilling off the solvent
  9. customthe obtained residue was purified by column chromatography (silica gel, hexane/ether)

Sources & evidence

ORD record
ord-267ef0259dfb45a39cdbaa999896445a
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

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