Trimethylamine oxide → 2,2-Dimethyl-6-oxohexanenitrile

HRID 76299

Reaction equation

HRID 76299 reaction equation
C[N+]([O-:5])(C)C.Br[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]#[N:13]>CS(C)=O>[CH3:14][C:11]([CH3:15])([CH2:10][CH2:9][CH2:8][CH:7]=[O:5])[C:12]#[N:13]

Participants

4

Reactant 2

HCID 1145Trimethylamine oxideHCID 46382156-Bromo-2,2-dimethylhexanenitrile

Product 1

HCID 866263532,2-Dimethyl-6-oxohexanenitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of trimethylamine oxide (1.5 g, 19.6 mmol, Aldrich) in DMSO (10 mL) was added 6-bromo-2,2-dimethylhexanenitrile (0.84 mL, 4.9 mmol, Aldrich). After stirring at room temperature overnight, the reaction mixture was quenched with water (10 mL) and extracted with hexanes (4×10 mL). The combined organic extracts were washed with brine (20 mL), dried (NaSO4), filtered and concentrated to afford 0.65 g (80% pure) of the title compound. MS (ESI+) m/z 157 (M+NH4)+.

Workup

  1. customthe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with hexanes (4×10 mL)
  3. washThe combined organic extracts were washed with brine (20 mL)
  4. dry with materialdried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e8db837b5104b6794378b445eb20a15
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Linked notes

Loading…