Ethyl formate → Ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionate

HRID 637918

Reaction equation

HRID 637918 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[CH3:2].[CH2:15]([O:17]C=O)C.[H-].[Na+].C(OCC)(=O)C>COCCOC>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([CH:15]=[O:17])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8025Ethyl formateHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 3018102Ethyl 3-(6-methyl-3-pyridyl)propionate

Product 1

HCID 3018359Ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 16.0 g (0.083 mole) of 3-(6-methyl-3-pyridyl)-propionic acid ethyl ester and 9.6 g (0.13 mole) of formic acid ethyl ester is slowly added dropwise while cooling with ice to a suspension of 5.2 g of sodium hydride (80% on paraffin oil; 0.17 mole) in 30 ml of ethylene glycol dimethyl ether. On completion of the addition, the solution is stirred for 8 hours at room temperature. After the addition of 10 ml of ethyl acetate and 200 ml of ice water, the mixture is extracted three times with diethyl ether. The aqueous phase is diluted to pH 5.4 with dilute hydrochloric acid and the crystals precipitating are filtered under suction. Light brown crystals melting at 141°-142° C. are obtained in a yield of 12.8 g (70%).

Workup

  1. additionis slowly added dropwise
  2. additionOn completion of the addition
  3. extractionthe mixture is extracted three times with diethyl ether
  4. additionThe aqueous phase is diluted to pH 5.4 with dilute hydrochloric acid
  5. customthe crystals precipitating
  6. filtrationare filtered under suction

Sources & evidence

ORD record
ord-88b44feb8dfb4474ab98ff99fe37d769
Source dataset
uspto-grants-1985_12
Patent number
US04559344

Linked notes

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