Water → HCID 11009692, compound

HRID 275757Notes

Reaction equation

HRID 275757 reaction equation
COC(=O)[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:5](=[O:12])[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.[Cl-].[Na+].O>CS(C)=O>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:4][C:5]([C:6]2[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=2)=[O:12])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 5234Sodium ChlorideHCID 54318349HCID 54318349, compound

Product 1

HCID 11009692HCID 11009692, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(4-methoxyphenyl)-3-oxo-3-(pyridin-4-yl)propionic acid methyl ester (14.7 g), sodium chloride (6.0 g) and water (1.9 cm3) in dimethyl sulphoxide (200 cm3) was stirred at 150° C. for 2 hours. The solution was cooled to room temperature, poured into water (600 cm3) and extracted with ethyl acetate-diethyl ether (1:1; 2×400 cm3). The extracts were dried (magnesium sulphate), filtered and concentrated to give 2-(4-methoxyphenyl)-1-(pyridin-4-yl)ethanone as a brown solid (10.2 g; 87%). δH (250 MHz; CDCl3) 3.79 (3 H, s, OCH3), 4.44 [2 H, s, C(O)CH2Ar], 6.88 (2 H, d, J 9, methoxyphenyl H-2), 7.16 (2 H, d, J 9, methoxyphenyl H-3), 7.77 (2 H, d, J 6, pyridyl H-3) and 8.80 (2 H, d, J 6, pyridyl H-2).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with ethyl acetate-diethyl ether (1:1; 2×400 cm3)
  3. dry with materialThe extracts were dried (magnesium sulphate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b2c3e0a6fc6b442ba56c87e25fae39e2
Source dataset
uspto-grants-2002_03
Patent number
US06352994B2

Reaction notes

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