4,4-Dibenzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione → 4,4-Dibenzyl-1,7-diphenylheptane-3,5-dione

HRID 714163ノート

反応式

HRID 714163 の反応式
[CH2:1]([C:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:19](=[O:28])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9](=[O:18])[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[CH2:29]([C:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:19](=[O:28])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9](=[O:18])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

参加物

4

反応物 1

HCID 695017744,4-Dibenzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione

生成物 1

HCID 588334354,4-Dibenzyl-1,7-diphenylheptane-3,5-dione収率 86%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

4,4-Dibenzyl-1,7-diphenyl-1, 6-heptadiene-3,5-dione (12b, 70 mg, 0.2 mmol) and palladium on activated carbon (0.10 g, 10%) were combined in ethyl acetate (25 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 5 hr at room temperature. The resulting mixture was filtered through celite and the filtrate was washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was chromatographed on silica gel with ethyl acetate/hexane to give a solid. The solid was recrystallized from hexane to give 60 mg (86%) of a white solid: mp 101-102° C. [expected mp 100.5-101.5° C.]; 1H NMR: δ 2.56 (t, 4H, J=7.4 Hz), 2.74 (t, 4H, J=6.8 Hz), 3.29 (s, 4H), 7.04 (m, 20H); 13C NMR: δ 29.6, 37.3, 42.5, 71.1, 126.1, 126.8, 128.4, 129.6, 136.0, 140.6, 207.8; Anal. Calcd for C33H32O2: C, 86.05; H, 7.00. Found: C, 86.28; H, 7.11.

後処理

  1. customfor 5 hr
  2. customat room temperature
  3. filtrationThe resulting mixture was filtered through celite
  4. washthe filtrate was washed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a solid
  9. customThe crude solid was chromatographed on silica gel with ethyl acetate/hexane
  10. customto give a solid
  11. customThe solid was recrystallized from hexane

出典と根拠

ORDレコード
ord-4b61a0e116e54357bfdaf9e17cb1af31
出典データセット
uspto-grants-2015_11
特許番号
US09187397B2

反応ノート

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