Acetonitrile → 5,5-dimethyl-3-oxohexanenitrile

HRID 2109923Notes

Reaction equation

HRID 2109923 reaction equation
[C:1](#[N:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:14][C:15]([CH3:22])([CH3:21])[CH2:16][C:17](OC)=[O:18].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:14][C:15]([CH3:22])([CH3:21])[CH2:16][C:17](=[O:18])[CH2:2][C:1]#[N:3]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 66298Methyl 3,3-dimethylbutyrateHCID 516892Sodium BicarbonateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 289056125,5-dimethyl-3-oxohexanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 500 mL dried round-bottom flask, acetonitrile (6.31, 153.6 mmol) dissolved in THF (50 mL) was treated with LiHMDS (156.3 mL, 1.0 M solution in THF) at −78° C. To this solution was added methyl 3,3-dimethylbutanoate in THF (50 mL) at −78° C. The solution was warmed to rt, and NaHCO3 (100 mL, saturated solution) was added. The layers were separated and the aqueous layer was extracted with ether (3×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product, which was used in the next step without purification. 1H NMR (300 MHz, CD2Cl2) δ 3.47 (s, 2H), 2.44 (s, 2H), 1.03 (s, 9H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ether (3×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-979a7f53ce2a474da52880b5bb630f61
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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