Methanol → HCID 15296555、化合物

HRID 2210074ノート

反応式

HRID 2210074 の反応式
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

参加物

6

反応物 3

HCID 887MethanolHCID 19379910(E)-7-(Phenylmethoxy)-8-(3-phenyl-2-propenyl)-4H-1-benzopyran-4-oneHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 15296555HCID 15296555、化合物収率 228.9%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9e820fffd8424a9aa16ab3dd7e94aa13
出典データセット
uspto-grants-1995_10
特許番号
US05457124

反応ノート

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