Acetonitrile → HCID 11769906, compound

HRID 1625185Notes

Reaction equation

HRID 1625185 reaction equation
[C:1](#[N:3])[CH3:2].[C:4](=[O:6])=O.[CH2:7]([OH:9])[CH3:8].[CH2:10]([Li])[CH2:11][CH2:12][CH3:13]>CCCCCC.C1COCC1>[OH:9][C:7]1([CH2:2][C:1]#[N:3])[C:10]2[C:11](=[CH:10][CH:11]=[C:12]([O:6][CH3:4])[CH:13]=2)[CH2:12][CH2:13][CH2:8]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 19604758Methanedione--ethanol (1/1)HCID 178418339Butyllithium

Product 1

HCID 11769906HCID 11769906, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a reaction vessel was added acetonitrile (19.0 ml) and anhydrous THF (50 ml), cooled to −70° C. with dry ice/ethanol, then the solution of n-Butyl Lithium in n-hexane (2.5 M, 142.0 ml) was added dropwise slowly. After stirring for half an hour under this temperature, the solution of the compound II (44.6 g) in anhydrous THF (300 ml) was added dropwise slowly, and stirred for 1 h at the same temperature. The reaction is quenched by adding saturated aqueous ammonium chloride (700 ml), extracted with ethyl acetate (350 ml×3). The organic layers were combined, washed with saturated aqueous NaCl (350 ml), dried over anhydrous sodium sulfate, and concentrated to obtain the off-white title product (54.3 g). Yield: 98.3%.

Workup

  1. stirringstirred for 1 h at the same temperature
  2. customThe reaction is quenched
  3. additionby adding saturated aqueous ammonium chloride (700 ml)
  4. extractionextracted with ethyl acetate (350 ml×3)
  5. washwashed with saturated aqueous NaCl (350 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-de8e4ca7788743969c6d3b8d0d9e7253
Source dataset
uspto-grants-2014_07
Patent number
US08779199B2

Reaction notes

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