Sodium hydride → HCID 178506156, 화합물

HRID 381442노트

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HRID 381442 반응식
[H-].[Na+].[Cl-].[F:4][C:5]([F:35])([F:34])[C:6]1[CH:33]=[CH:32][C:9](/[CH:10]=[CH:11]/[CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1.[Cl:36][C:37]1[CH:52]=[CH:51][C:40]([CH2:41][S:42][C@H:43]2[CH2:48][CH2:47][C@H:46]([CH:49]=O)[CH2:45][CH2:44]2)=[CH:39][CH:38]=1>CCCCCC.CS(C)=O.C1(C)C=CC=CC=1>[F:35][C:5]([F:4])([F:34])[C:6]1[CH:7]=[CH:8][C:9](/[CH:10]=[CH:11]/[CH:12]=[CH:49]/[C@H:46]2[CH2:45][CH2:44][C@H:43]([S:42][CH2:41][C:40]3[CH:51]=[CH:52][C:37]([Cl:36])=[CH:38][CH:39]=3)[CH2:48][CH2:47]2)=[CH:32][CH:33]=1

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 18367709[(E)-4-(trifluoromethyl)cinnamyl]triphenylphosphonium chlorideHCID 178520994HCID 178520994, 화합물

생성물 1

HCID 178506156HCID 178506156, 화합물수율 31.2%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 1140Toluene용매HCID 8058Hexane용매

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온도
55 °C

실험 절차

After 50 mg (1.14 mmol) of 55% sodium hydride were washed with hexane, it was suspended in 7 ml of dimethyl sulfoxide, followed by stirring of the suspension at 55° C. for 2.5 hours. The mixture was cooled to room temperature and 607 mg (1.26 mmol) of [(E)-4-(trifluoromethyl) cinnamyl]triphenylphosphonium chloride were added thereto. Further, 170 mg (0.63 mmol) of trans-4-[(4-chlorobenzyl) thio]cyclohexanecarboxaldehyde were added to the resulting mixture, followed by stirring of the mixture at room temperature for 15 minutes. The mixture was diluted with toluene and washed with water and an aqueous NaCl solution. After the mixture was dried, the crude product obtained by evaporation of the solvent was subjected to column chromatography using 5 g of silica gel and eluted with a mixed solvent of methylene chloride-hexane (1:2). The eluted portion was recrystallized from hexane to obtain 86 mg (yield: 31%) of the title compound having a melting point of 142 to 144° C.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. stirringby stirring of the mixture at room temperature for 15 minutes
  3. washwashed with water
  4. customAfter the mixture was dried
  5. customthe crude product obtained by evaporation of the solvent
  6. washeluted with a mixed solvent of methylene chloride-hexane (1:2)
  7. customThe eluted portion was recrystallized from hexane

출처 및 근거

ORD 기록
ord-94ea31e2caee4a3699cf8f6f0d605500
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306880B1

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