Water → 4'-Pentyl-bicyclohexyl-4-carboxylic acid 6-(2-methyl-acryloyloxy)-hexyl ester

HRID 386324Notes

Reaction equation

HRID 386324 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]([CH:19]1[CH2:24][CH2:23][CH:22]([CH:25]2[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:27][CH2:26]2)[CH2:21][CH2:20]1)=[O:18].O>CN(C)C=O>[CH3:3][C:2](=[CH2:4])[C:1]([O:6][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]([CH:19]1[CH2:20][CH2:21][CH:22]([CH:25]2[CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:27][CH2:26]2)[CH2:23][CH2:24]1)=[O:18])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 4093Methacrylic AcidHCID 24758Sodium hydrideHCID 592890424'-Pentyl-bicyclohexyl-4-carboxylic acid 6-bromo-hexyl ester

Product 1

HCID 592890404'-Pentyl-bicyclohexyl-4-carboxylic acid 6-(2-methyl-acryloyloxy)-hexyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of methacrylic acid (3.6 g, 41.8 mmol) in dimethylformamide (30 ml) is added dropwise to an ice cooled slurry of sodium hydride (60% suspension in paraffin oil) (1.5 g, 37.5 mmol) in dimethylformamide (50 ml). Once addition is complete, the mixture is allowed to warm to room temperature and is stirred for 1 h, the intermediate 4′-pentyl-bicyclohexyl-4-carboxylic acid 6-bromo-hexyl ester (15.0 g, 33.8 mmol) in dimethylformamide (100 ml) is added dropwise. The mixture is stirred at 50° C. over night. The mixture is cooled to room temperature, poured into icy water, and this is extracted three times with DCM. The DCM solution is washed with brine, water and then dried over sodium sulphate. The solution is evaporated to dryness and recrystallised from acetonitrile to afford a white waxy solid. Further purification is achieved by preparative HPLC using water/acetonitrile as eluant.

Workup

  1. additionOnce addition
  2. stirringThe mixture is stirred at 50° C. over night
  3. temperatureThe mixture is cooled to room temperature
  4. extractionthis is extracted three times with DCM
  5. washThe DCM solution is washed with brine, water
  6. dry with materialdried over sodium sulphate
  7. customThe solution is evaporated to dryness
  8. customrecrystallised from acetonitrile
  9. customto afford a white waxy solid
  10. customFurther purification

Sources & evidence

ORD record
ord-20399f3c8b2b4a9d9914604b169a4c07
Source dataset
uspto-grants-2013_02
Patent number
US08372307B2

Reaction notes

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