Dimethylformamide → 1a,7b-Dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carboxaldehyde

HRID 1030210Notes

Reaction equation

HRID 1030210 reaction equation
Br[C@H:2]1[C@H:7]([OH:8])[C:6]2[CH:9]=[C:10]([CH:13]=[O:14])[CH:11]=[CH:12][C:5]=2[O:4][C:3]1([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:15][C:3]1([CH3:16])[CH:2]2[O:8][CH:7]2[C:6]2[CH:9]=[C:10]([CH:13]=[O:14])[CH:11]=[CH:12][C:5]=2[O:4]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 13704275HCID 13704275, compound

Product 1

HCID 137042811a,7b-Dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carboxaldehydeYield 58.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of trans-3-bromo-3,4-dihydro-2,2-dimethyl-4-hydroxy-2H-1-benzopyran-6-carbaldehyde (6.9 g), potassium carbonate (6.7 g), and dimethylformamide (24 ml) was stirred at room temperature for 48 hours and followed by at 35° C. for 24 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by recrystallization from diisopropyl ether to give 3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-1-benzopyran-6-carbaldehyde (2.9 g).

Workup

  1. waitfollowed by at 35° C. for 24 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-48fdf6e283364909b8404b22e04bef0a
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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