2,9-dimethoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one → 8-Methoxypsoralen

HRID 66071Notes

Reaction equation

HRID 66071 reaction equation
CO[CH:3]1[O:18][C:6]2=[C:7]([O:16][CH3:17])[C:8]3[O:13][C:12](=[O:14])[CH:11]=[CH:10][C:9]=3[CH:15]=[C:5]2[CH2:4]1>C(O)=O>[CH3:17][O:16][C:7]1[C:8]2[O:13][C:12](=[O:14])[CH:11]=[CH:10][C:9]=2[CH:15]=[C:5]2[CH:4]=[CH:3][O:18][C:6]=12

Participants

3

Reactant 1

HCID 203802262,9-dimethoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one

Product 1

HCID 41148-Methoxypsoralen

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 0.253 g. (1.02 mmoles) of 2,9-dimethoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one in 10 ml. of formic acid was heated at 100° for 40 min. The reaction was cooled and evaporated. The residue was filtered through alumina using benzene/ethyl acetate, 4:1 to yield, upon evaporation of the filtrate, pure 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one, mp 145°-146°.

Workup

  1. temperatureThe reaction was cooled
  2. customevaporated
  3. filtrationThe residue was filtered through alumina

Sources & evidence

ORD record
ord-755c2f9d40ed40c7bedeb16b10220fe0
Source dataset
uspto-grants-1978_12
Patent number
US04130568

Reaction notes

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