Water → 3,4-epoxy-2,2-diethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

HRID 704780Notes

Reaction equation

HRID 704780 reaction equation
Br[C@H:2]1[C@H:7]([OH:8])[C:6]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:5]=2[O:4][C:3]1([CH2:17][CH3:18])[CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:8]1[CH:7]2[CH:2]1[C:3]([CH2:17][CH3:18])([CH2:15][CH3:16])[O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:6]=12

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 14721186trans-3-bromo-2,2-diethyl-3,4-dihydro-4-hydroxy-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 147211883,4-epoxy-2,2-diethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrileYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of trans-3-bromo-2,2-diethyl-3,4-dihydro-4-hydroxy-2H-1-benzopyran-6-carbonitrile (1.95 g) and potassium carbonate (1.74 g) in N,N-dimethylformamide (8 ml) was stirred overnight at ambient temperature. The reaction mixture was poured into water, extracted with ethyl acetate, and then washed with water and brine successively. The extract was dried over anhydrous magnesium sulfate, treated with active charcoal, and evaporated in vacuo. The residue was purified with silica gel column chromatography using a mixture of methylene chloride and n-hexane (1:2) as an eluent to give 3,4-epoxy-2,2-diethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrile (1.17 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and brine successively
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. additiontreated with active charcoal
  5. customevaporated in vacuo
  6. customThe residue was purified with silica gel column chromatography
  7. additiona mixture of methylene chloride and n-hexane (1:2) as an eluent

Sources & evidence

ORD record
ord-6beefcbb421c483e99c6659e609cab70
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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