Sodium hydride → HCID 178506156, compound

HRID 381442Notes

Reaction equation

HRID 381442 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 178506156HCID 178506156, compoundYield 31.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
55 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-94ea31e2caee4a3699cf8f6f0d605500
Source dataset
uspto-grants-2001_10
Patent number
US06306880B1

Reaction notes

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