Water → HCID 54159118, compound

HRID 465534Notes

Reaction equation

HRID 465534 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].C([Li])CCC.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]=O)[CH:35]=1.O>CS(C)=O.C1COCC1.C(OCC)(=O)C>[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])[CH:35]=1

Participants

8

Reactant 4

HCID 962WaterHCID 103713-PyridinecarboxaldehydeHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 178418339Butyllithium

Product 1

HCID 54159118HCID 54159118, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 69 g of 5-carboxypentyl-triphenylphosphonium bromide in a mixture of 125 ml of DMSO and 250 ml THF cooled to 20° is added 130 ml of a 2.4M solution of n-butyllithium dropwise over a period of 30 min. After stirring for 45 min, a solution of 10.7 g 3-pyridine-carboxaldehyde in 25 ml of THF is added dropwise, then the solution is stirred for 1 h before adding water and ethyl acetate. The aqueous layer is separated, acidified to pH 6 and extracted with ethyl acetate. The ethyl acetate extract is dried over magnesium sulfate, filtered and concentrated to give 7-(3-pyridyl)-hept-6-enoic acid which is converted to methyl 7-(3-pyridyl)-hept-6-enoate by refluxing in methanolic hydrochloric acid.

Workup

  1. temperaturecooled to 20°
  2. stirringthe solution is stirred for 1 h
  3. customThe aqueous layer is separated
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. dry with materialis dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9e646be09e35457b897c0e711152bb5b
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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