Dimethyl Sulfoxide → 7,7-Diphenylhept-6-enoic acid

HRID 1651218

반응식

HRID 1651218 반응식
[H-].[Na+].CS(C)=O.[Br-].[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[C:35]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O1CCCC1>[C:36]1([C:35]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 3102BenzophenoneHCID 24758Sodium hydrideHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromide

생성물 1

HCID 3364807,7-Diphenylhept-6-enoic acid수율 70.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The reaction was carried out as in Example 87 using the following reagents: sodium hydride (56% dispersion in oil; 8.6 g); dimethylsulfoxide (100 mL), (5-carboxypentyl)triphenylphosphonium bromide (37.64 g); benzophenone (18 g) and tetrahydrofuran (100 mL). The acid, isolated in the normal manner, was crystallized from hexane to give 16.3 g of 7,7-diphenyl-6-heptenoic acid, mp 71.5°-72.5° C. A portion was recrystallized from hexane to give the analytical sample, mp 72.5°-73.5° C. Anal. Calculated for C19H20O2 : C, 81.40; H, 7.19. Found: C, 81.61; H, 7.40.

후처리

  1. customThe acid, isolated in the normal manner
  2. customwas crystallized from hexane

출처 및 근거

ORD 기록
ord-3fd35f1fca6a408a90b075a3dea125e5
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04927838

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