Carbon Dioxide → 2-Cyano-3-isopropyl-hexanoic acid methyl ester

HRID 1795560Notes

Reaction equation

HRID 1795560 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].C(=O)=O>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

6

Reactant 4

HCID 280Carbon DioxideHCID 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

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-cyano-4-methyl-2-pentenoic acid (3.0 g, 19.6 mmol) in 50 mL of THF which is cooled in an EPA/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-4da0b5c304494afbbccce1768ccf7819
Source dataset
uspto-grants-2006_04
Patent number
US07026505B2

Reaction notes

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