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

HRID 374825Notes

Reaction equation

HRID 374825 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].CC(C)([O-])C.[K+].C(NC1C=C([C:44]2[C:49]([C:50]([C:52]3[C:53]([C:58]4C=CC=[C:60]([NH:64][C:65](=[O:67])[CH3:66])[CH:59]=4)=NC=C[CH:57]=3)=O)=[CH:48][CH:47]=[CH:46][N:45]=2)C=CC=1)(=O)C.O>O1CCCC1>[C:65]([NH:64][C:60]1[CH:57]=[C:52]([C:50]([C:49]2[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=2)=[CH:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])[CH:53]=[CH:58][CH:59]=1)(=[O:67])[CH3:66]

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

To a mixture of 217 g of 4-carboxybutyl-triphenylphosphonium bromide and 154 g of potassium tert.butoxide in 1.8 liters of tetrahydrofuran are added, at -25° C., 94 g of 3-acetylaminophenyl-3-pyridyl ketone. After 2 hours stirring at ambient temperature the reaction mixture is combined with 200 ml of water and then substantially evaporated down. The residue is taken up in 500 ml of water and washed with ethyl acetate. The aqueous 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. additionare added, at -25° C.
  2. customsubstantially evaporated down
  3. washwashed with ethyl acetate
  4. additionThe aqueous phase is then neutralised by the addition of citric acid
  5. extractionextracted with ethyl acetate
  6. customThe organic phase is evaporated down
  7. customthe residue is recrystallised from ethyl acetate/acetone

Sources & evidence

ORD record
ord-0bc1f5315ad34ca48e606dd262ce8542
Source dataset
uspto-grants-1996_01
Patent number
US05482948

Reaction notes

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