Tetrahydrofuran → (E)-4-(4-(1,2-dihydro-2-oxo-1-pyridyl)phenyl)-3-butenoic acid

HRID 1769666Notes

Reaction equation

HRID 1769666 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[Cl-].[C:17]([CH2:20][CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:19])=[O:18].O1CCCC1.CC(C)([O-])C.[K+]>O>[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C:8]1[CH:15]=[CH:14][C:11](/[CH:12]=[CH:21]/[CH2:20][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 10270534(2-Carboxyethyl)triphenylphosphonium chlorideHCID 107031494-(2-oxo-2H-pyridin-1-yl)-benzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 15045332(E)-4-(4-(1,2-dihydro-2-oxo-1-pyridyl)phenyl)-3-butenoic acidYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-50 °C

Procedure

3.00 g of 4-(1,2-dihydro-2-oxo-1-pyridyl)benzaldehyde and 6.15 of β-carboxyethyltriphenyl phosphonium chloride were suspended into 30 ml of tetrahydrofuran, cooled to -50° C. and stirred. 20 ml of a tetrahydrofuran solution of 3.72 g of potassium-tert-butoxide was dropped and the temperature was gradually raised to 0° C. After 10 hours, iced water was added and the aqueous layer was washed with ether. The aqueous layer was adjusted to about pH 3 with concentrated hydrochloric acid, and deposited crystals were collected by filtration to obtain 2.96 g of the above-captioned compound as pale brown yellow powder (yield: 77%). Melting point (°C.): 218.5-221.5

Workup

  1. temperaturethe temperature was gradually raised to 0° C
  2. washthe aqueous layer was washed with ether
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f46a0153927e44bea975d31760c0bade
Source dataset
uspto-grants-1995_01
Patent number
US05382595

Reaction notes

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