2H-1-Benzopyran, 6-methoxy- → HCID 131715140, compound

HRID 979155Notes

Reaction equation

HRID 979155 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH:9]=[CH:8][C:7]=2[CH:12]=1.[N+](=[C:15]([C:20]([O:22][CH3:23])=[O:21])[C:16]([O:18][CH3:19])=[O:17])=[N-]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C@@H:9]3[C:15]([C:20]([O:22][CH3:23])=[O:21])([C:16]([O:18][CH3:19])=[O:17])[C@@H:8]3[C:7]=2[CH:12]=1

Participants

4

Reactant 2

HCID 290522H-1-Benzopyran, 6-methoxy-HCID 5476732-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olate

Product 1

HCID 131715140HCID 131715140, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To stirred solution of 79 g of 6-methoxy-2H-[1]benzopyran (J. Org. Chem. 1973, 38, 3832) and 17.6 g of cuprous iodide-trimethyl phosphite (Synthesis 1971, 658) in 400 ml toluene, is added at 103° 125 g dimethyl diazomalonate (Synthesis 1971, 658) over a period of 30 min. After stirring 1.5 h, the reaction mixture is cooled, filtered through Celite, concentrated under reduced pressure and flash chromatographed with ethyl acetate/hexane (3:7) to give cis-(±)-dimethyl 1,1a,2,7b-tetrahydro-6-methoxybenzo[b]cyclopropa[d]pyran-1,1-dicarboxylate.

Workup

  1. temperaturethe reaction mixture is cooled
  2. filtrationfiltered through Celite
  3. concentrationconcentrated under reduced pressure and flash
  4. customchromatographed with ethyl acetate/hexane (3:7)

Sources & evidence

ORD record
ord-e176d1ad75c644eeaf32774c71ee0ac7
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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