Methanol → HCID 15296555, compound

HRID 2210074Notes

Reaction equation

HRID 2210074 reaction equation
C1(C[O:8][C:9]2[CH:19]=[CH:18][C:12]3[C:13](=[O:17])[CH:14]=[CH:15][O:16][C:11]=3[C:10]=2[CH2:20]/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)C=CC=CC=1.CO.[H][H]>[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:19]=[CH:18][C:12]2[C:13](=[O:17])[CH2:14][CH2:15][O:16][C:11]=2[C:10]=1[CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 19379910(E)-7-(Phenylmethoxy)-8-(3-phenyl-2-propenyl)-4H-1-benzopyran-4-oneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 15296555HCID 15296555, compoundYield 228.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6.1 g (16.6 mmol) of (E)-7-(phenylmethoxy)-8-(3-phenyl-2-propenyl)-4H-1-benzopyran-4-one from the preceding example, 1 g of 10% palladium on carbon, 100 mL of methanol, and 300 mL of ethyl acetate was stirred at room temperature, in an atmosphere of hydrogen until approximately one third of the theoretical volume of hydrogen gas was taken up. The catalyst was filtered with suction and the filtrate concentrated in vacuo. The residue was dissolved in 150 mL of methanol and 0.5 g of Raney nickel was added. The hydrogenation was continued with careful monitoring by TLC analysis. When the reduction was essentially complete, the catalyst was filtered with suction and the filtrate concentrated in vacuo. The solid residue (4.75 g) was combined with 6.4 g from another experiment (23.9 mmol scale) and chromatographed on silica gel. Elution with hexane-ethyl acetate mixtures afforded 10.73 g (93.9%) of the title compound as a colorless solid, mp 110°-112° C.

Workup

  1. filtrationThe catalyst was filtered with suction
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in 150 mL of methanol
  4. addition0.5 g of Raney nickel was added
  5. filtrationthe catalyst was filtered with suction
  6. concentrationthe filtrate concentrated in vacuo
  7. customchromatographed on silica gel
  8. washElution with hexane-ethyl acetate mixtures

Sources & evidence

ORD record
ord-9e820fffd8424a9aa16ab3dd7e94aa13
Source dataset
uspto-grants-1995_10
Patent number
US05457124

Reaction notes

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