Water → HCID 54159118, compound

HRID 1494077Notes

Reaction equation

HRID 1494077 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 69g 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 minutes. After stirring for 45 minutes a solution of 10.7g 3-pyridine-carboxaldehyde in 25 mL of THF is added dropwise, then the solution is stirred for 1 hour 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. additionis added dropwise
  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-2c5d4e8e6df24846b069c7c8d2e0ec39
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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