Hydrochloric Acid → HCID 19392519, compound

HRID 1755989Notes

Reaction equation

HRID 1755989 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[CH:8][N:7]=1)=[CH2:5])C.Cl>CC(C)=O>[C:4]([C:6]1[N:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[CH:8][N:7]=1)(=[O:3])[CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19392525HCID 19392525, compound

Product 1

HCID 19392519HCID 19392519, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 1-ethoxy-1-(4-ethoxypyrimidin-2-yl)-ethylene (2.7 g) in acetone (20 ml) was treated with hydrochloric acid (6 ml of a 2M solution). The reaction mixture was allowed to stand for 16 hours, then warmed at 40° C. for 11/2 hours, and concentrated. The residue was diluted with water and neutralised with sodium bicarbonate. The aqueous phase was extracted with ethyl acetate (×2) and the combined extracts were washed with brine, dried and concentrated to give 2-acetyl-4-ethoxypyrimidine (1.8 g, 78% yield) as a colourless oil which partially solidified on standing, and was used without further purification; IR maximum (film): 1717cm-1 ; 1H NMR (270 MHz): δ1.45(3H,t), 2.74(3H,s), 4.53(2H,q), 6.85(1H,d), 8.60(1H,d) ppm.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with water and neutralised with sodium bicarbonate
  3. extractionThe aqueous phase was extracted with ethyl acetate (×2)
  4. washthe combined extracts were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ad20cd99e7cd44e4b6671e2395a830bc
Source dataset
uspto-grants-1995_08
Patent number
US05439910

Reaction notes

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