Potassium tert-butoxide → HCID 18968199, compound

HRID 399588Notes

Reaction equation

HRID 399588 reaction equation
CC(C)([O-])C.[K+].[C:7]([C@:9]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)([CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])#[N:8]>CS(C)=O>[C:7]([C:9]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)([CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])#[N:8]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 53841069HCID 53841069, compound

Product 1

HCID 18968199HCID 18968199, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium tert-butoxide (27.5 mg, 0.25 mmol) was added to a solution of methyl (S)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoate (150 mg, 0.491 mmol; 97% ee by chiral HPLC analysis) in anhydrous dimethyl sulphoxide (4 ml). The resulting golden yellow solution was stirred at room temperature for five minutes and then heated at 100° C. for 1 hour. The reaction mixture was then worked up by quenching with acetic acid and evaporation of solvent under high vacuum, followed by partitioning of the residue between methyl tert-butyl ether and water. The washed and dried organic extract was concentrated to provide methyl 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoate as an oil (60 mg; 40% recovery). Chiral HPLC analysis of a sample removed prior to heating the reaction mixture at 100° C. showed methyl (S)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoate of substantially reduced enantiomeric purity (ca. 10% ee).

Workup

  1. temperatureheated at 100° C. for 1 hour
  2. customby quenching with acetic acid and evaporation of solvent under high vacuum
  3. customby partitioning of the residue between methyl tert-butyl ether and water
  4. washThe washed
  5. extractiondried organic extract
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-183a1b7808f241d5bf96d99e746001a6
Source dataset
uspto-grants-1998_10
Patent number
US05821369

Reaction notes

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