HCID 11805918, compound → 2-Phenyl-3,4-dihydro-2H-1-benzopyran

HRID 1462955Notes

Reaction equation

HRID 1462955 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)(=O)C.[C].[Pd]>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 11805918HCID 11805918, compound

Product 1

HCID 941562-Phenyl-3,4-dihydro-2H-1-benzopyran

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

The flav-3-ene was catalytically hydrogenated in acetic acid (60 ml) using 10% palladium carbon catalyst (150 mg) at room temperature and a atmospheric pressure. 750 ml hydrogen was absorbed over 3 hr. The reaction mixture was filtered, diluted with water, extracted with toluene, and the evaporated extract chromatographed on neutral alumina, eluting with toluene. The product was recrystallised from ethanol yielding flavan (2.75 g) m.pt. 43°-44° C.

Workup

  1. customat room temperature
  2. custom750 ml hydrogen was absorbed over 3 hr
  3. filtrationThe reaction mixture was filtered
  4. additiondiluted with water
  5. extractionextracted with toluene
  6. extractionthe evaporated extract
  7. customchromatographed on neutral alumina
  8. washeluting with toluene
  9. customThe product was recrystallised from ethanol

Sources & evidence

ORD record
ord-e163519bfdc04366996388da1b5f07d7
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

Loading…