Methyl vinyl ketone → Ethyl 2-cyano-2-methyl-5-oxohexanoate

HRID 481795

Reaction equation

HRID 481795 reaction equation
[C:1]([CH:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[CH:10]([C:12]([CH3:14])=[O:13])=[CH2:11]>C1(C)C=CC=CC=1>[O:13]=[C:12]([CH3:14])[CH2:10][CH2:11][C:3]([C:1]#[N:2])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 98018Ethyl 2-cyanopropionate

Product 1

HCID 10997948Ethyl 2-cyano-2-methyl-5-oxohexanoateYield 86.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 127 mg (1.0 mmol) of ethyl 2-cyanopropanoate, 0.12 ml (1.5 mmol) of methyl vinyl ketone, and 9.4 mg (0.01 mmol) of Rh(acac)(CO)(L) obtained in Example 8 was stirred in 5 ml of toluene at 0° C. for 13 hours. The reaction mixture was concentrated to yield 170 mg (86%) of ethyl 5-oxo-2-cyano-2-methylhexanoate. The product was found to have an optical purity of 73% e.e. as analyzed by high performance liquid chromatography using a Chiralcel OJ column manufactured by Daicel Chemical Industries, Ltd.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-49a72e9593ab433e9ab931ca2b9cc5be
Source dataset
uspto-grants-1998_08
Patent number
US05789609

Linked notes

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