m-Chloroperbenzoic acid → HCID 13632649, compound

HRID 280389Notes

Reaction equation

HRID 280389 reaction equation
[OH:1][C:2]([C:5]1([C:11]#[N:12])[CH2:9][CH:8]=[C:7]([CH3:10])[CH2:6]1)([CH3:4])[CH3:3].ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[OH:1][C:2]([C:5]1([C:11]#[N:12])[CH2:9][CH:8]2[C:7]([CH3:10])([O:21]2)[CH2:6]1)([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13632648HCID 13632648, compound

Product 1

HCID 13632649HCID 13632649, compoundYield 111.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred mixture of 11.65 g of 1-(1-hydroxy-1-methylethyl)-3-methyl-3-cyclopentene-1-carbonitrile in 700 ml of methylene chloride and 210 ml of aqueous sodium bicarbonate was added portionwise at 25°-35° C. 15.3 g of 85% m-chloroperbenzoic acid. After stirring overnight, the phases were separated and the organic phase was washed successively with 200 ml of 1N sodium hydroxide, 200 ml of water and 200 ml of saturated aqueous sodium chloride, dried (MgSO4), and concentrated in vacuo to leave 14.2 g of a colorless oil, as a 1.2;1.0 mixture of diastereomeric epoxides. These diastereomers were separated by flash silica gel column chromatography using 2:8:40 tetrahydrofuran/ethyl acetate/hexane as eluent to give 5.1 g of the less polar (1α,3β,5α) isomer as a colorless oil and using 2:15:33 ratio of the same solvents to give 5.4 g of the more polar (1α,3α,5α)isomer as a colorless oil.

Workup

  1. additionwas added portionwise at 25°-35° C
  2. customthe phases were separated
  3. washthe organic phase was washed successively with 200 ml of 1N sodium hydroxide, 200 ml of water and 200 ml of saturated aqueous sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ec0de304fcb469cb200814a15d6e3cf
Source dataset
uspto-grants-1986_05
Patent number
US04588821

Reaction notes

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