Methanol → HCID 15296555, 화합물

HRID 2210074노트

반응식

HRID 2210074 반응식
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

참가 물질

6

반응물 3

HCID 887MethanolHCID 19379910(E)-7-(Phenylmethoxy)-8-(3-phenyl-2-propenyl)-4H-1-benzopyran-4-oneHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 15296555HCID 15296555, 화합물수율 228.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e820fffd8424a9aa16ab3dd7e94aa13
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05457124

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