Hydrochloric Acid → HCID 15857586, compound

Participants

Reaction Conditions

Reaction Steps

a 100 mL three necked RB flask, equipped with a rubber septum, a teflon coated stir bar and a gas inlet adaptor was flushed with N2. 4′-methyl-2,2′:6′,2″-terpyridine (18) (0.494 gm., 2 mmol), prepared by literature methods (see K. T. Potts, et al, J. Am. Chem. Soc., 1987, 109, 3961-3967) was dissolved in dry THF (10 mL) and was syringed into the flask. The reaction mixture was cooled to −78° C. and LDA (1.6 mL, 2.4 mmol) was added via syringe. The resulting dark brown mixture was stirred for 2 hr. at −78° C. 2-(2-bromoethyl)-1,3-dioxolane (0.434 mL, 2.4 mmol) was syringed into the reaction mixture, stirred for 1 hr. at −78° C. and allowed to warm to room temperature overnight. The mixture was poured over 10 ml brine and the aqueous layer was extracted with CH2Cl2. The extracts were dried over MgSO4 and evaporated to dryness to yield the crude acetal. The acetal was hydrolyzed with 1M HCl (10 mL) by heating to 50-60° C. for 2 hours. The solution was then neutralized with aqueous NaHCO3 and extracted with CH2Cl2. The extracts were dried over MgSO4 and evaporated to dryness to yield the crude aldehyde. Purification by flash chromatography (neutral alumina, CH2Cl2 elution) gave pure aldehyde (19) (0.339 gm., 1.12 mmol, 56%).

Provenance & Evidence