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

HRID 714157

反応式

HRID 714157 の反応式
[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

参加物

4

反応物 1

HCID 390472Dicinnamoylmethane

生成物 1

HCID 101493901,7-Diphenylheptane-3,5-dione収率 71.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a3507acaa51240ab9e508d842305df9a
出典データセット
uspto-grants-2015_11
特許番号
US09187397B2

関連ノート

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