m-Chloroperbenzoic acid → 3-(3,4-Dichlorophenyl)-3,4-epoxy-1-butanol t-butyldimethylsilyl ether

HRID 1275161Notes

Reaction equation

HRID 1275161 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)=[CH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[OH:22].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][C:11]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[O:22][CH2:12]1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 108712633-(3,4-Dichlorophenyl)-3-butenol t-butyldimethylsilyl ether

Product 1

HCID 572763533-(3,4-Dichlorophenyl)-3,4-epoxy-1-butanol t-butyldimethylsilyl etherYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.00 g (9.05 mmole) of 3-(3,4-dichlorophenyl)-3-butenol t-butyldimethylsilyl ether [prepared as described in Example 1(b)] were dissolved in 60 ml of methylene chloride, and 2.52 g (30.0 mmole) of sodium hydrogencarbonate and 3.88 g (15.7 mmole) of 3-chloroperbenzoic acid (content: 70%) were added to the resulting solution. The mixture was then stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was diluted with methylene chloride and then washed with a 1 N aqueous solution of sodium hydroxide and with a saturated aqueous solution of sodium chloride. The organic layer was then dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reduced pressure. The resulting residue was then purified by silica gel column chromatography, using a gradient elution method, with mixtures of hexane and diethyl ether ranging from 24:1 to 19:1 by volume as the eluent, to obtain 2.70 g of the title compound.

Workup

  1. washwashed with a 1 N aqueous solution of sodium hydroxide and with a saturated aqueous solution of sodium chloride
  2. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customThe resulting residue was then purified by silica gel column chromatography
  5. washa gradient elution method

Sources & evidence

ORD record
ord-4d59ea19cd3d412dbe6fbf48f19a7aa2
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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