Ethanol → Diethyl (1-cyano-3-methylbutyl)propanedioate

HRID 1094918Notes

Reaction equation

HRID 1094918 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@H:6]([C:11]#[N:12])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2].CCO.[O-]CC.[Na+]>CC(O)=O>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]([C:11]#[N:12])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 11565095HCID 11565095, compound2×

Product 1

HCID 11666030Diethyl (1-cyano-3-methylbutyl)propanedioate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A reactor was charged with (R)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid ethyl ester (Formula 22, 49.5 kg) and EtOH (250 L). Sodium ethoxide (21% w/w in EtOH, 79.0 L, 1.1 eq) was added to the mixture, which was heated to 80° C. for 20 h. After completion of the reaction, the mixture was allowed to cool to RT and was neutralized by adding HOAc (12.2 L). Following evaporation of the EtOH, MTBE (150 L) was added to the mixture, and the resulting solution was filtered and evaporated to afford (R/S)-3-cyano-2-ethoxycarbonyl-5-methyl-hexanoic acid ethyl ester (Formula 20) in quantitative yield.

Workup

  1. customAfter completion of the reaction
  2. temperatureto cool to RT
  3. customevaporation of the EtOH, MTBE (150 L)
  4. additionwas added to the mixture
  5. filtrationthe resulting solution was filtered
  6. customevaporated

Sources & evidence

ORD record
ord-d8775632a4924165a3c06f44530a85b5
Source dataset
uspto-grants-2012_03
Patent number
US08134023B2

Reaction notes

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