Pyridine → HCID 86749650, compound

HRID 1735708Notes

Reaction equation

HRID 1735708 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:5].C(OCC)(OCC)O[CH2:17][CH3:18].N1C=CC=C[CH:26]=1>C(O)C.S(=O)(=O)(O)O>[CH2:17]([O:5]/[C:4](/[C:3]1[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=1[CH3:1])=[CH:6]/[C:7]([O:9][CH2:10][CH3:26])=[O:8])[CH3:18]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31214Ethyl orthoformateHCID 2760278Methyl 3-(2-methylphenyl)-3-oxopropanoate

Product 1

HCID 86749650HCID 86749650, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

19.2 g (100 mmol) of methyl 2-methylbenzoylacetate and 17.7 g of triethyl orthoformate in 40 ml of ethanol plus 0.4 ml of concentrated sulfuric acid are refluxed for 16 hours. After cooling, 2 ml of pyridine are added and the mixture is then concentrated. The residue is taken up in methyl t-butyl ether and extracted 2×with water. The organic phase is dried over sodium sulfate and concentrated. The crude product contains in addition to the title compound about 15% of the corresponding (E) methyl ester (Compound No. 1.47). Distillation results in 16.5 g (75%) of the title compound as colorless oil. 1H-NMR (CDCl3): δ=1.05 (3H, t); 1.37 (3H, t); 2.25 (3H, s); 3.97 (2H, q); 3.99 (2H, q); 5.32 (1H, s); 7.1-7.3 (4H, m) ppm.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is then concentrated
  3. extractionextracted 2×with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated
  6. additionThe crude product contains in addition to the title compound about 15% of the corresponding (E) methyl ester (Compound No
  7. distillationDistillation

Sources & evidence

ORD record
ord-7088874aaccb4627b35c9bc6ea13db5d
Source dataset
uspto-grants-1996_07
Patent number
US05538940

Reaction notes

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