Acetonitrile → Methyl (RS)-4-cyano-2-phenylbutanoate

HRID 486487

Reaction equation

HRID 486487 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9](#[N:11])[CH3:10].[C:12]1([C:18](=[CH2:23])[C:19]([O:21][CH3:22])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>C1CCCCC1.O1CCCC1>[C:9]([CH2:10][CH2:23][CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:19]([O:21][CH3:22])=[O:20])#[N:11]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 25517Ammonium ChlorideHCID 193334Methyl atropateHCID 2724682Lithium diisopropylamide

Product 1

HCID 53645094Methyl (RS)-4-cyano-2-phenylbutanoateYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

Lithium diisopropylamide (3.67 ml of a 1.5 molar solution in cyclohexane) was added to acetonitrile (0.26 ml) in tetrahydrofuran (10 ml) at -78° C. After 1 hour, methyl 2-phenyl-acrylate (see Preparation 22) (0.81 g) in tetrahydrofurn (10 ml) was added and the mixture was stirred for 1 hour, allowed to warm to room temperature then treated with saturated ammonium chloride solution. The resulting mixture was partitioned between ethyl acetate and water, the organic phase dried over magnesium sulphate and evaporated to give a residue which was partitioned between ether and 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulphate and evaporated to leave the title compound (0.5 g, 75%) as an oil.

Workup

  1. customThe resulting mixture was partitioned between ethyl acetate and water
  2. dry with materialthe organic phase dried over magnesium sulphate
  3. customevaporated
  4. customto give a residue which
  5. customwas partitioned between ether and 10% aqueous sodium carbonate
  6. dry with materialThe organic layer was dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-80af75f55504407f8422051aeb00f6fc
Source dataset
uspto-grants-1994_03
Patent number
US05292749

Linked notes

Loading…