Dicinnamoylmethane → 1,7-Diphenylheptane-3,5-dione

HRID 77642

반응식

HRID 77642 반응식
[C:1]1([CH:7]=[CH:8][C:9](=[O:21])[CH2:10][C:11](=[O:20])[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(OCC)(=O)C>[C:14]1([CH2:13][CH2:12][C:11](=[O:20])[CH2:10][C:9](=[O:21])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

4

반응물 1

HCID 390472Dicinnamoylmethane

생성물 1

HCID 101493901,7-Diphenylheptane-3,5-dione수율 71.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

1,7-Diphenyl-1,6-heptadiene-3,5-dione (3b, 0.56 g, 2.0 mmol) and palladium on activated carbon (0.25 g, 5%) were combined in ethyl acetate (40 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 4 hr at room temperature. The resulting mixture was filtered through celite and the solvent evaporated to afford an oil. The crude oil was purified by preparative thin layer chromatography with ethyl acetate/hexane to give 0.40 g (70%) of an orange-yellow oil; 1H NMR: δ enol form: 2.53 (m, 4H), 2.83 (m, 4H), 5.47 (s, 1H), 7.30 (m, 10H); keto form: 2.53 (m, 4H), 2.83 (m, 4H), 3.54 (s, 2H), 7.30 (m, 10H); 13C NMR: δ 29.4, 31.5, 39.9, 45.0, 99.5, 126.1, 128.3, 128.5, 140.5, 170.4, 172.0, 192.8.

후처리

  1. customfor 4 hr
  2. customat room temperature
  3. filtrationThe resulting mixture was filtered through celite
  4. customthe solvent evaporated
  5. customto afford an oil
  6. customThe crude oil was purified by preparative thin layer chromatography with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-be5b5c4af19f47388d31ee34b103f170
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841326B2

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