Methyl phenylacetate → Methyl 3-cyano-2-phenylpropanoate

HRID 323292

Reaction equation

HRID 323292 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:12]([N-:15]C(C)C)(C)[CH3:13].[Li+].BrCC#N>O1CCCC1>[C:12]([CH2:13][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:15]

Participants

5

Reactant 3

HCID 7559Methyl phenylacetateHCID 11534BromoacetonitrileHCID 2724682Lithium diisopropylamide

Product 1

HCID 18464584Methyl 3-cyano-2-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine methyl phenylacetate (2.0 g, 13.32 mmol) and tetrahydrofuran (15 mL). Cool in a dry-ice/acetone bath. Add dropwise a solution of lithium diisopropylamide (6.66 mL, 2 M in THF, 13.32 mmol). After 1 hour, add α-bromoacetonitrile (1.6 g, 13.32 mmol). After 2 hours, warm the reaction mixture to ambient temperature and partition the reaction mixture between ethyl acetate and water. Separate the aqueous layer and extract three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Distill the residue bulb-to-bulb to give the title compound: bp; 150° C. at 0.5 mm Hg; Rf=0.72 (silica gel, 25% ethyl acetate/hexane).

Workup

  1. temperatureCool in a dry-ice/acetone bath
  2. waitAfter 2 hours
  3. custompartition the reaction mixture between ethyl acetate and water
  4. customSeparate the aqueous layer
  5. extractionextract three times with ethyl acetate
  6. dry with materialDry the combined organic layers over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto obtain a residue
  10. distillationDistill the residue bulb-to-bulb

Sources & evidence

ORD record
ord-94c4d080b6c14409865112be5c287e5b
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Linked notes

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