Water → 6-(3-Acetylaminophenyl)-6-(3-pyridyl)hex-5-enoic acid

HRID 1975387Notes

Reaction equation

HRID 1975387 reaction equation
C(NC1C=C([C:11]2[C:16]([C:17]([C:19]3[C:20]([C:25]4C=CC=[C:27]([NH:31][C:32](=[O:34])[CH3:33])[CH:26]=4)=NC=C[CH:24]=3)=O)=[CH:15][CH:14]=[CH:13][N:12]=2)C=CC=1)(=O)C.[Br-].[C:36]([CH2:39][CH2:40][CH2:41][CH2:42][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:38])=[O:37].CC(C)([O-])C.[K+].O>O1CCCC1>[C:32]([NH:31][C:27]1[CH:24]=[C:19]([C:17]([C:16]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:42][CH2:41][CH2:40][CH2:39][C:36]([OH:38])=[O:37])[CH:20]=[CH:25][CH:26]=1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 53837382HCID 53837382, compound

Product 1

HCID 537920006-(3-Acetylaminophenyl)-6-(3-pyridyl)hex-5-enoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At -25° C., 94 g of 3-acetylaminophenyl-3-pyridylketone are added to a mixture of 217 g of 4-carboxybutyl-triphenylphosphonium bromide and 154 g of potassium tert.butoxide in 1.8 litres of tetrahydrofuran. After 2 hours stirring at ambient temperature, 200 ml of water are added to the reaction mixture and then it is evaporated down. The residue is taken up in 500 ml of water and washed with ethyl acetate. The agueous phase is then neutralised by the addition of citric acid and extracted with ethyl acetate. The organic phase is evaporated down and the residue is recrystallised from ethyl acetate/acetone.

Workup

  1. customit is evaporated down
  2. washwashed with ethyl acetate
  3. additionThe agueous phase is then neutralised by the addition of citric acid
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is evaporated down
  6. customthe residue is recrystallised from ethyl acetate/acetone

Sources & evidence

ORD record
ord-ac5d55fd01ee45708cfb4cc65905a7fe
Source dataset
uspto-grants-1994_02
Patent number
US05286736

Reaction notes

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