Methyl 9-oxononanoate → HCID 86758897, compound

HRID 1263949Notes

Reaction equation

HRID 1263949 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[CH3:6][O:7][C:8](=[O:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=O>CS(C)=O>[CH3:6][O:7][C:8](=[O:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:3][C:2]#[CH:1]

Participants

4

Reactant 2

HCID 74732Methyl 9-oxononanoateHCID 178418339Butyllithium

Product 1

HCID 86758897HCID 86758897, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

n-Butyl lithium (750 μL, 2M) was added methyl sulfoxide (6 mL) under argon at room temperature. The solution was stirred for half an hour, and (3-trimethylsillyl-2-propynyl)-triphenylphosphonium bromide (1 mmole) in methyl sulfoxide was added and stirred for one hour. 9-Oxo-nonanoic acid methyl ester in methyl sulfoxide was added to the reaction mixture and stirred for 4.5 hours. The reaction mixture was poured onto ice water and extracted with ethyl acetate three times. The organic layers were combined and dried to obtain crude mixture, which was further purified through Si gel column chromatography. The product contained trans and cis isomers in about 8:2 ratio.

Workup

  1. stirringstirred for one hour
  2. stirringstirred for 4.5 hours
  3. additionThe reaction mixture was poured onto ice water
  4. extractionextracted with ethyl acetate three times
  5. customdried
  6. customto obtain crude mixture, which
  7. customwas further purified through Si gel column chromatography

Sources & evidence

ORD record
ord-e21768e9fbb047479758931356f7d122
Source dataset
uspto-grants-2003_04
Patent number
US06541506B1

Reaction notes

Loading…