Psoralen → 4',5'-Dihydropsoralen

HRID 1708208Notes

Reaction equation

HRID 1708208 reaction equation
[CH:1]1[C:5]2=[CH:6][C:7]3[CH:14]=[CH:13][C:11](=[O:12])[O:10][C:8]=3[CH:9]=[C:4]2[O:3][CH:2]=1.C1CCCCC=1>C(O)C.[Pd]>[CH2:1]1[C:5]2[CH:6]=[C:7]3[C:8](=[CH:9][C:4]=2[O:3][CH2:2]1)[O:10][C:11](=[O:12])[CH:13]=[CH:14]3

Participants

5

Reactant 2

HCID 6199PsoralenHCID 8079Cyclohexene

Product 1

HCID 1514674',5'-DihydropsoralenYield 72.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution was prepared of 1.86 g (0.010 moles) of psoralen (7H-furo[3,2-g][1]benzopyran-7-one) in 200 ml of 95% ethanol, heated to reflux and treated by the addition of 5.0 ml of cyclohexene and a slurry of 5.0 g of 10% palladium on carbon in 30 ml of 95% ethanol. After 30 minutes of reflux with magnetic stirring the medium was filtered, evaporated in vacuo and the residue was recrystallized from 95% ethanol to give 1.36 g (72% yield) of tiny white needles, mp 198°-200° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureAfter 30 minutes of reflux
  4. filtrationwas filtered
  5. customevaporated in vacuo
  6. customthe residue was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-69e848c5b8824399a57e364330f4c1d4
Source dataset
uspto-grants-1994_10
Patent number
US05356929

Reaction notes

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