Water → 5,5-Dimethyl-3-formyl-hexanoic acid methyl ester

HRID 1663557Notes

Reaction equation

HRID 1663557 reaction equation
C(NCC(C)C)C(C)C.[CH3:10][C:11]([CH3:17])([CH3:16])[CH2:12][CH2:13][CH:14]=[O:15].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].O>C1(C)C=CC=CC=1>[CH3:23][O:22][C:20](=[O:21])[CH2:19][CH:13]([CH:14]=[O:15])[CH2:12][C:11]([CH3:17])([CH3:16])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8085DiisobutylamineHCID 60984Methyl bromoacetateHCID 110623434,4-Dimethylpentanal

Product 1

HCID 235310795,5-Dimethyl-3-formyl-hexanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a three necked flask fitted with a Dean-Stark apparatus under argon, a solution of diisobutylamine (4.62 ml from Acros), 4,4-dimethyl pentanal 362 (2.5 g, 0.021 mol.) in toluene (20 ml) is heated at 130° C. for 2 h and water is extracted. The yellow solution is cooled down to room temperature and methyl bromoacetate (3.7 g, 0.024 mol.) is added in one time. The pink solution is stirred at room temperature overnight and 1 h at 90° C. Water (10 ml) is added at this temperature and after 1 h, the solution is cooled down to room temperature. The organic layer is washed with HCl 1N, saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and evaporated to afford an oil which is distilled under reduced pressure (1 mmHg) to afford 5,5-dimethyl-3-formyl-hexanoic acid methyl ester 361 as a liquid (1.1 g, 0.05 mol, Teb (1 mmHg): 69-71° C.). The aldehyde esters are then used in the reductive amination step.

Workup

  1. customIn a three necked flask fitted with a Dean-Stark apparatus under argon
  2. extractionwater is extracted
  3. temperaturethe solution is cooled down to room temperature
  4. washThe organic layer is washed with HCl 1N, saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford an oil which
  9. distillationis distilled under reduced pressure (1 mmHg)

Sources & evidence

ORD record
ord-e4322e985dba43a6b8e30fe93c21960a
Source dataset
uspto-grants-2011_10
Patent number
US08034958B2

Reaction notes

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