Diphenyl Ether → 9-Methoxy-2-methyl-7h-furo[3,2-g]chromen-7-one

HRID 1448518Notes

Reaction equation

HRID 1448518 reaction equation
[CH3:1][CH:2]1[O:17][C:5]2=[C:6]([O:15][CH3:16])[C:7]3[O:12][C:11](=[O:13])[CH:10]=[CH:9][C:8]=3[CH:14]=[C:4]2[CH2:3]1.C1(OC2C=CC=CC=2)C=CC=CC=1>[Pd]>[CH3:16][O:15][C:6]1[C:7]2[O:12][C:11](=[O:13])[CH:10]=[CH:9][C:8]=2[CH:14]=[C:4]2[CH:3]=[C:2]([CH3:1])[O:17][C:5]=12

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 203802232-methyl-9-methoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one

Product 1

HCID 1653069-Methoxy-2-methyl-7h-furo[3,2-g]chromen-7-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 0.70 g. (3.02 mmoles) of 2-methyl-9-methoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one in 15 ml. of diphenyl ether was added 0.70 g. of 10% Pd/C. The mixture was heated under reflux for 6.0 hours, cooled, and filtered over Celite (washing with methanol). The methanol was removed from the filtrate by rotary evaporation, and the remaining solution of the product in diphenyl ether was diluted with 200 ml. of pet. ether. After standing overnight, the solid which separated was filtered off and washed with pet. ether to yield 9-methoxy-2-methyl-7H-furo[3,2-g][1]benzopyran-7-one. Recrystallization from ethanol afforded an analytical sample, mp 149°-150°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6.0 hours
  3. temperaturecooled
  4. filtrationfiltered over Celite (washing with methanol)
  5. customThe methanol was removed from the filtrate by rotary evaporation
  6. additionthe remaining solution of the product in diphenyl ether was diluted with 200 ml
  7. customthe solid which separated
  8. filtrationwas filtered off
  9. washwashed with pet. ether

Sources & evidence

ORD record
ord-7cd132baa8c945c6b94a061603f711fe
Source dataset
uspto-grants-1979_12
Patent number
US04180659

Reaction notes

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