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

HRID 77640

反応式

HRID 77640 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.[OH-].[Na+].O.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:25]([C:10]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:11](=[O:20])[CH:12]=[CH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:9](=[O:21])[CH:8]=[CH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

7

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 390472Dicinnamoylmethane

生成物 1

HCID 695017744,4-Dibenzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione収率 121.7%

試薬・触媒・溶媒 2

HCID 70681Tetrabutylammonium Chloride触媒HCID 6344Dichloromethane溶媒

実験手順

1,7-Diphenyl-1,6-heptadiene-3,5-dione (3b, 0.25 g, 0.9 mmol) was stirred in dichloromethane (4 ml) for 5 min at room temperature. A solution of sodium hydroxide (80.0 mg, 2.0 mmol), tetrabutylammonium chloride (0.29 g, 1.0 mmol) and water (2 ml) was added and the mixture stirred for 10 min at room temperature. Benzyl bromide (10, 0.22 ml, 1.8 mmol) was added and the mixture stirred for 1 hr at 40° C. The resulting mixture was cooled to room temperature, 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 methanol to give 0.25 g (61%) of a white solid: mp 182-183° C. [expected mp 181° C.]; 1H NMR: δ 3.39 (s, 4H), 6.70 (d, 2H, J=15.5 Hz), 7.09-7.44 (m, 20H), 7.73 (d, 2H, J=15.5 Hz); 13C NMR: δ 37.7, 70.3, 123.1, 126.7, 128.1, 128.6, 128.8, 130.3, 130.7, 134.2, 136.3, 142.7, 196.8.

後処理

  1. stirringthe mixture stirred for 1 hr at 40° C
  2. temperatureThe resulting mixture was cooled to room temperature
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was chromatographed on silica gel with ethyl acetate/hexane
  9. customto give a solid
  10. customThe solid was recrystallized from methanol

出典と根拠

ORDレコード
ord-8a38490a28ae40eab48e52fdb789b460
出典データセット
uspto-grants-2014_09
特許番号
US08841326B2

関連ノート

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