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

HRID 714155

反応式

HRID 714155 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-c64a444d3f1f4c898cdab58c7e7ba27b
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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