Ethanol → HCID 178450337, compound

HRID 542664Notes

Reaction equation

HRID 542664 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]=[CH:10][C:11](=[O:13])[CH3:12])=[C:4]([CH3:14])[N:3]=1.[C:15](OCC)(=O)[CH2:16][C:17]([O:19]CC)=O.[Na].[OH-].[K+].[C:29](=O)(O)[O-].[K+].[CH2:34]([OH:36])[CH3:35]>>[OH:36][C:34]1[CH2:35][CH:9]([C:5]2[C:6]([CH3:8])=[N:7][C:2]([CH3:1])=[N:3][C:4]=2[CH3:14])[CH2:10][C:11](=[O:13])[C:12]=1[C:17](=[O:19])[CH2:16][CH2:15][CH3:29]

Participants

6

Reactant 5

HCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 516893Potassium BicarbonateHCID 53774209HCID 53774209, compoundHCID 86602522HCID 86602522, compound

Product 1

HCID 178450337HCID 178450337, compound

Conditions

Temperature
100 °C

Procedure

and (iii) 1-(2,4,6-Trimethylpyrimidin-5-yl)but-1-en-3-one (1.5 g) and sodium diethyl malonate (2.5 equiv) were heated at reflux in absolute ethanol (40 ml) for 13 hr. A dilute aqueous potassium hydroxide solution (4 equiv) was added and the mixture was heated allowing the ethanol to distill off over 4 hr. The hot solution was made just acid by slow addition of a dilute hydrochloric acid solution. Potassium bicarbonate (2equiv) was added and the solvent was evaporated by reduced pressure distillation. The solid residue was thoroughly dried (100° C.; 0.1 mmHg). The residue was extracted with hot anhydrous dimethylformamide (40 ml). The soluble fraction was heated at 100° C. under nitrogen with butyric anhydride (3 ml) for 2 hr. The dimethylformamide (40 ml) was evaporated by reduced pressure distillation and the residue was shaken with a little dilute acetic acid. The whole mixture was extracted into ethyl acetate. The dried (MgSO4) solvent was evaporated and the residue was purified by column chromatography over silica gel with ethyl acetate elution to give 3-hydroxy-5-(2,4,6-trimethylpyrimidin-5-yl)-2-butyrylcyclohex-2-en-1-one as an oil. Pmr spectrum (CDCl3 ; δ in ppm): 1.01 (3H, t); 1.69 (2H, m); 2.3-3.9 (7H, m); 2.57 (6H, s); 2.63 (3H, s); 18.33 (1H, s).

Workup

  1. temperaturethe mixture was heated
  2. distillationto distill off over 4 hr
  3. additionby slow addition of a dilute hydrochloric acid solution
  4. customthe solvent was evaporated by reduced pressure distillation
  5. customThe solid residue was thoroughly dried (100° C.; 0.1 mmHg)
  6. extractionThe residue was extracted with hot anhydrous dimethylformamide (40 ml)
  7. customThe dimethylformamide (40 ml) was evaporated by reduced pressure distillation
  8. extractionThe whole mixture was extracted into ethyl acetate
  9. dry with materialThe dried (MgSO4) solvent
  10. customwas evaporated
  11. customthe residue was purified by column chromatography over silica gel with ethyl acetate elution

Sources & evidence

ORD record
ord-0590e4a287454a15bc363ffb5e153c59
Source dataset
uspto-grants-1987_04
Patent number
US04659362

Reaction notes

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