2-Ethyl-6-(1-hydroxypropan-2-yl)-4H-1-benzopyran-4-one → 2-(2,3-dihydro-2-ethyl-4-oxo-4H-1-benzopyran-6-yl)propanol

HRID 26678Notes

Reaction equation

HRID 26678 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:17])[CH2:15][OH:16])=[CH:10][C:6]=2[C:7](=[O:9])[CH:8]=1)[CH3:2]>C(O)C.[Ni]>[CH2:1]([CH:3]1[CH2:8][C:7](=[O:9])[C:6]2[CH:10]=[C:11]([CH:14]([CH3:17])[CH2:15][OH:16])[CH:12]=[CH:13][C:5]=2[O:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 127698102-Ethyl-6-(1-hydroxypropan-2-yl)-4H-1-benzopyran-4-one

Product 1

HCID 213219962-(2,3-dihydro-2-ethyl-4-oxo-4H-1-benzopyran-6-yl)propanolYield 108.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

2-(2-Ethyl-4-oxo-4H-1-benzopyran-6-yl)propan-1-ol (4.1 g) was taken up in ethanol (100 ml), Raney Nickel (5.0 g) was added and the mixture hydrogenated at 45 psi for 2 hours. The catalyst was removed by filtration (Hyflo supercel) and replaced with a fresh batch (5.0 g) and hydrogenation at 45 psi continued for a further 3 hours. The catalyst was removed by filtration and the filtrate evaporated to yield 2-(2,3-dihydro-2-ethyl-4-oxo-4H-1-benzopyran-6-yl)propanol as a pale green oil (4.5 g), I.R. carbonyl absorption 1690 cms-1.

Workup

  1. customThe catalyst was removed by filtration (Hyflo supercel)
  2. waitcontinued for a further 3 hours
  3. customThe catalyst was removed by filtration
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-c0e3dc6ad52d4314b49fdafdbb6c9675
Source dataset
uspto-grants-1979_04
Patent number
US04151179

Reaction notes

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