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

HRID 486487

Reaktionsgleichung

Reaktionsgleichung von HRID 486487
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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-80af75f55504407f8422051aeb00f6fc
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292749

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