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

HRID 714155

반응식

HRID 714155 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.[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

참가 물질

7

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 390472Dicinnamoylmethane

생성물 1

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

시약·촉매·용매 2

HCID 70681Tetrabutylammonium Chloride촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c64a444d3f1f4c898cdab58c7e7ba27b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187397B2

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