Diethyl Ether → 2-Cyano-3-isopropyl-hexanoic acid methyl ester

HRID 479074Notes

Reaction equation

HRID 479074 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH3:3].[CH3:6]COCC.[C:11]([C:13](=[CH:17][CH:18]([CH3:20])[CH3:19])[C:14]([OH:16])=[O:15])#[N:12]>C1COCC1>[CH3:6][O:15][C:14](=[O:16])[CH:13]([C:11]#[N:12])[CH:17]([CH:18]([CH3:20])[CH3:19])[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2925472-Cyano-4-methylpent-2-enoic acidHCID 178455855HCID 178455855, compound

Product 1

HCID 541521852-Cyano-3-isopropyl-hexanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

A 2.0 M solution of propyl magnesium chloride in Et2O (9.8 mL, 19.6 mmol) is added to a solution of 2-cyano4-methyl-2-pentenoic acid (3.0 g, 19.6 mmol) in 50 mL of THF which is cooled in an IPA/dry ice bath to −40° C. under argon. The solution is stirred for 4 hours, and the reaction is quenched by addition of 50 mL of saturated KH2PO4. The THF is evaporated, and the remaining oil is chromatographed under medium pressure over silica gel with 50% CH2Cl2/hexane. Yield=1.9 g (50%) of 2-cyano-3-isopropyl-hexanoic acid methyl ester as an oil.

Workup

  1. customthe reaction is quenched by addition of 50 mL of saturated KH2PO4
  2. customThe THF is evaporated
  3. customthe remaining oil is chromatographed under medium pressure over silica gel with 50% CH2Cl2/hexane

Sources & evidence

ORD record
ord-95663f39283f40eebdf4a2bdf8748c20
Source dataset
uspto-grants-2003_11
Patent number
US06642398B2

Reaction notes

Loading…