4-Pyridinecarboxaldehyde → HCID 86654331, compound

Participants

Reaction Steps

[(3-Nitro-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-phosphonic acid dimethyl ester (40.7 g, 0.105 mol) was dissolved in dry THF (1 L) under nitrogen. Sodium hydride (60% suspension in mineral oil) (6.3 g, 0.158 mol, 1.5 eq) was added and the mixture was stirred for 10 minutes at room temperature. Neat 4-picolinaldehyde (10 mL, 0.105 mol, 1 eq) was then added dropwise and the mixture was heated to 60° C. and stirred at this temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure to ⅓ of the original volume and then diluted with water (500 mL). pH was adjusted to 7-8 by adding a saturated solution of NaHCO3 and the mixture was extracted with ethyl acetate (4×300 mL). The organic layer was dried over Na2SO4 and concentrated to dryness. An oil (37.7 g) was obtained, which was used without further purification in the following step.

Provenance & Evidence