m-Chloroperbenzoic acid → 3,4-epoxy-2,2-diethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

HRID 1460623Notes

Reaction equation

HRID 1460623 reaction equation
[CH2:1]([C:3]1([CH2:15][CH3:16])[CH:8]=[CH:7][C:6]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:5]=2[O:4]1)[CH3:2].C(=O)(O)[O-:18].[Na+].ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[CH2:15]([C:3]1([CH2:1][CH3:2])[CH:8]2[O:18][CH:7]2[C:6]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:5]=2[O:4]1)[CH3:16]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 147211802,2-Diethyl-2h-chromene-6-carbonitrile

Product 1

HCID 147211883,4-epoxy-2,2-diethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12 g of the above chromene are dissolved in 400 ml of abs. dichloromethane, the obtained solution is mixed with anhydrous sodium bicarbonate and oxidized during 3 days with 31 mg of m-chloroperbenzoic acid. The slightly yellow suspension is partitioned between an aq. ammoniumhydroxide solution (5%) and dichlormethane, the organic phases are washed with water and dried over sodiumsulphate. The oil, obtained after concentration, is purified by flash-chromatography (silica gel/dichloromethane, hexane 2:3). Besides of educt, 2,2-diethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran-6-carbonitrile is obtained as colorless oil.

Workup

  1. customThe slightly yellow suspension is partitioned between an aq. ammoniumhydroxide solution (5%) and dichlormethane
  2. washthe organic phases are washed with water
  3. dry with materialdried over sodiumsulphate
  4. customThe oil, obtained
  5. concentrationafter concentration
  6. customis purified by flash-chromatography (silica gel/dichloromethane, hexane 2:3)

Sources & evidence

ORD record
ord-50380f93ed114136a56007d90d775be5
Source dataset
uspto-grants-1991_12
Patent number
US05071871

Reaction notes

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