Acetonitrile → HCID 59267900, compound

HRID 1802409Notes

Reaction equation

HRID 1802409 reaction equation
CO[C:3](=[O:18])[C:4]([CH3:17])([CH3:16])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.[C:19](#[N:21])[CH3:20].[H-].[Na+]>C1(C)C=CC=CC=1.Cl>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][O:6][CH2:5][C:4]([CH3:16])([CH3:17])[C:3](=[O:18])[CH2:20][C:19]#[N:21])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 11054128HCID 11054128, compound

Product 1

HCID 59267900HCID 59267900, compoundYield 104.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 3.66 g (14.5 mmol) of 2,2-dimethyl-3-(4-methoxybenzyl-oxy)-propionic acid methyl ester and 1.07 mL (20.5 mmol) of acetonitrile in anhydrous toluene (10 mL) is added dropwise to a refluxing suspension of 0.83 g (20.5 mmol) of sodium hydride (60% dispersion in mineral oil) in toluene (20 mL). After the addition is complete, the mixture is stirred at reflux for 3 h, then allowed to cool to room temperature. The reaction mixture is then diluted with 1M aqueous HCl solution to neutral pH, and extracted with ethyl acetate (3×40 mL). The combined organic extracts are washed with water and brine, then dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure to afford 3.95 g of 5-(4-methoxy-benzyloxy)-4,4-dimethyl-3-oxo-pentanenitrile, which is used in the next step without further purification. Yield: assumed quantitative, no spectroscopic analysis performed.

Workup

  1. additionAfter the addition
  2. temperatureat reflux for 3 h
  3. extractionextracted with ethyl acetate (3×40 mL)
  4. washThe combined organic extracts are washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-7949272964644206a5e7660a4e6dcd97
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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