diethyl 3,4-dihydro-4-oxo-7-hydroxy-8-propyl-2H-1-benzopyran-2,2-dipropanoate → diethyl 3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

HRID 2371627Notes

Reaction equation

HRID 2371627 reaction equation
O=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([OH:15])=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:3]1>C(O)(=O)C.[H][H].[Pd]>[CH2:12]([C:11]1[C:6]2[O:5][C:4]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:3][CH2:2][C:7]=2[CH:8]=[CH:9][C:10]=1[OH:15])[CH2:13][CH3:14]

Participants

5

Reactant 1

HCID 19756625diethyl 3,4-dihydro-4-oxo-7-hydroxy-8-propyl-2H-1-benzopyran-2,2-dipropanoate

Product 1

HCID 15157486diethyl 3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoateYield 19.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

The title product of Example 1 (4.19 g, 10.3 mmol) was dissolved in 50 ml of acetic acid, and then hydrogenated at 70° C. using 60 psi of hydrogen and 10% palladium on carbon as catalyst. After eight hours, the mixture was allowed to cool, and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure. The residue was chromatographed on silicagel column. Elution with 20% ethyl acetate/hexane afforded the title compound (0.80 g).

Workup

  1. customhydrogenated at 70° C.
  2. temperatureto cool
  3. custominsolubles were removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was chromatographed on silicagel column
  6. washElution with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9b633aeee933475fa98baf2bef216144
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

Loading…