Diethyl Ether → Methyl 2-formylisonicotinate

HRID 2254455Notes

Reaction equation

HRID 2254455 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:3][C:2]=1[C:11](OC)=[O:12].[H-].C([Al+]CC(C)C)C(C)C.C(OCC)C.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:11]([C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][N:1]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 254545Dimethyl pyridine-2,4-dicarboxylateHCID 21225700DiisobutylaluminumhydrideHCID 21226206Ethyl acetate hexane

Product 1

HCID 19744506Methyl 2-formylisonicotinateYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.07 g of dimethyl pyridine-2,4-dicarboxylate was dissolved in 20 ml of toluene, and with stirring under cooling at -80° to -70° C., 6.04 ml of a 1M toluene solution of diisobutylaluminium hydride was added dropwise over 2.5 hours, and the mixture was stirred at this temperature for 1 hour. The reaction mixture was poured into ice water, and ethyl ether was added. The organic layer was separated, worked up in a customary manner, and then purified by medium-pressure liquid chromatography Lobar column, size B, Lichroprep Si 60 (E. Merck Co.); eluting solvent: hexane/ethyl acetate=4/1→3/1) to give 0.27 g (yield 30%) of methyl 2-formylisonicotinate as a colorless crystalline powder.

Workup

  1. temperatureunder cooling at -80° to -70° C.
  2. stirringthe mixture was stirred at this temperature for 1 hour
  3. additionwas added
  4. customThe organic layer was separated
  5. custompurified by medium-pressure liquid chromatography Lobar column, size B, Lichroprep Si 60 (E. Merck Co.)

Sources & evidence

ORD record
ord-daf03e7bc6974d30a3606d18155f156a
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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