Ethanol → HCID 15099993, compound

HRID 358936Notes

Reaction equation

HRID 358936 reaction equation
[C:1]([C:3]([CH3:10])([CH2:7][CH2:8][CH3:9])[C:4]([OH:6])=[O:5])#[N:2].P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:22](O)[CH3:23]>>[C:1]([C:3]([CH3:10])([CH2:7][CH2:8][CH3:9])[C:4]([O:6][CH2:22][CH3:23])=[O:5])#[N:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 14793479HCID 14793479, compound

Product 1

HCID 15099993HCID 15099993, compoundYield 90%

Procedure

0.30 g (2.1 mM) of (-)-2-cyano-2-methylpentanoic acid was dissolved in 3 ml of dry ethanol. To the mixture under stirring, 0.49 g (3.2 mM) of phosphorus oxychloride was added dropwise. After the reaction for 3 hours at 80° C., 6 ml of 1N-sodium carbonate aqueous solution was added, followed by extraction with diethyl ether. The resultant ether solution was dried on anhydrous sodium sulfate, followed by distilling-off of the solvent and distillation to obtain 0.32 g (1.9 mM) of (-)-ethyl 2-cyano-2-methylpentanoate. Yield:90%, b.p.:110° C./22 mmHg, [α]D -3.0 degrees, [α]435 -4.5 degrees, (c1, methanol)

Workup

  1. customAfter the reaction for 3 hours at 80° C.
  2. extractionfollowed by extraction with diethyl ether
  3. dry with materialThe resultant ether solution was dried on anhydrous sodium sulfate
  4. distillationfollowed by distilling-off of the solvent and distillation

Sources & evidence

ORD record
ord-e25b360bf8e449738c8f995b0d0d46ad
Source dataset
uspto-grants-1991_03
Patent number
US04999130

Reaction notes

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