Pyridine → HCID 86749650, compound

HRID 1899792Notes

Reaction equation

HRID 1899792 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12].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:13]/[C:5](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=[CH:4]/[C:3]([O:2][CH2:1][CH3:26])=[O:14])[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 methyl2-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.

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-c068b6801b3d413ca532abd880dfa75c
Source dataset
uspto-grants-1996_11
Patent number
US05573999

Reaction notes

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