Sodium hydride → HCID 19776116, compound

HRID 1612610Notes

Reaction equation

HRID 1612610 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]([OH:29])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[H-].[Na+].[H][H].Br[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH:47]=[CH2:48])=[O:44]>C1(C)C=CC=CC=1>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]([O:29][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH:47]=[CH2:48])=[O:44])[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 19776099HCID 19776099, compoundHCID 19776105HCID 19776105, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19776116HCID 19776116, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.1 mol of 1-(4-propylcyclohexyl)-2-(4'-pentylbiphenyl-4-yl)-ethanol is stirred with 0.1 mol of sodium hydride in 350 ml of toluene at room temperature until evolution of hydrogen is complete. 0.1 mol of allyl 9-bromopelargonate (obtained from allyl bromide and 9-bromopelargonic acid in dimethylformamide using potassium carbonate) is then added, and the mixture is kept at 60° C. for 3 hours. After cooling, the mixture is washed with water and dried over sodium sulfate, and the solvent is removed under reduced pressure to give allyl 9-(1-(4-propylcyclohexyl)-2-(4'-pentylbiphenyl-4-yl)-ethoxy)-pelargonate.

Workup

  1. temperatureAfter cooling
  2. washthe mixture is washed with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-9cfea116cbc646be84c741b72387a730
Source dataset
uspto-grants-1993_03
Patent number
US05190689

Reaction notes

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