m-Chloroperbenzoic acid → 4-[4-(t-Butyldimethylsilyl)oxy-1,2-epoxy-2,6,6-trimethylcyclohexyl]but-3-en-2-one

HRID 703621Notes

Reaction equation

HRID 703621 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[C:12]([CH:17]=[CH:18][C:19](=[O:21])[CH3:20])=[C:11]([CH3:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[Si:1]([O:8][CH:9]1[CH2:14][C:13]([CH3:15])([CH3:16])[C:12]2([CH:17]=[CH:18][C:19](=[O:21])[CH3:20])[O:31][C:11]2([CH3:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 541718584-[4-(t-Butyldimethylsilyl)oxy-2,6,6-trimethylcyclohex-1-enyl]but-3-en-2-one

Product 1

HCID 543893744-[4-(t-Butyldimethylsilyl)oxy-1,2-epoxy-2,6,6-trimethylcyclohexyl]but-3-en-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 20 ml of an anhydrous chloroform solution containing 1.0 g of 4-[4-(t-butyldimethylsilyl)oxy-2,6,6-trimethylcyclohex-1-enyl]but-3-en-2-one was added 616 mg of m-chloroperbenzoic acid under ice-cooling, followed by stirring at the same temperature for 8 hours. After completion of the reaction, the reaction mixture was washed several times with a saturated aqueous solution of sodium hydrogen carbonate. The organic layer was washed with a saturated aqueous solution of sodium chloride and then, with water, and dried over anhydrous magnesium sulfate. The solvent, etc. were removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 644 mg (yield: 70%) of 4-[4-(t-butyldimethylsilyl)oxy-1,2-epoxy-2,6,6-trimethylcyclohexyl]but-3-en-2-one.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. washthe reaction mixture was washed several times with a saturated aqueous solution of sodium hydrogen carbonate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialwith water, and dried over anhydrous magnesium sulfate
  6. customThe solvent, etc. were removed by distillation under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1735545c59ca4eacb6ce023d14ed0d49
Source dataset
uspto-grants-1991_01
Patent number
US04983723

Reaction notes

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