Sodium hydride → HCID 178506156、化合物

HRID 1601380ノート

反応式

HRID 1601380 の反応式
[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

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 18367709[(E)-4-(trifluoromethyl)cinnamyl]triphenylphosphonium chlorideHCID 178520994HCID 178520994、化合物

生成物 1

HCID 178506156HCID 178506156、化合物収率 31.2%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 1140Toluene溶媒HCID 8058Hexane溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-30523b506ad242578a755a2388fda11b
出典データセット
uspto-grants-1999_11
特許番号
US05977152

反応ノート

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