methyl 3-(3,4-dihydro-7-hydroxy-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl)propanoate → methyl 3-(3,4-dihydro-7-hydroxy-2-methyl-8-propyl-2H-1-benzopyran-2-yl)propanoate

HRID 477507

Reaction equation

HRID 477507 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=O)[CH2:7][C:8]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])([CH3:10])[O:9][C:4]=2[C:3]=1[CH2:20][CH2:21][CH3:22]>C(O)(=O)C.CO.[Pd]>[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH2:7][C:8]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])([CH3:10])[O:9][C:4]=2[C:3]=1[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 1

HCID 2801556methyl 3-(3,4-dihydro-7-hydroxy-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl)propanoate

Product 1

HCID 14882982methyl 3-(3,4-dihydro-7-hydroxy-2-methyl-8-propyl-2H-1-benzopyran-2-yl)propanoateYield 45.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 4.1 g (13.4 mmole) of ester product of Example 4 in 100 ml of acetic acid and 50 ml of methanol was hydrogenated for 21 hours at 4 psi and room temperature using palladium on carbon as catalyst. The catalyst was filtered and the filtrate was evaporated to dryness. Chromatography of the residue on silica gel using 20% ethyl acetate/hexane as eluent gave 1.8 g of the title compound as an oil. Structure assignment was confirmed by nmr and infrared spectra.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-697e8087bd0a4304afa4102c97b28955
Source dataset
uspto-grants-1989_12
Patent number
US04888356

Linked notes

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