Triphenylphosphine → HCID 13824169, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cold, mechanically stirred solution of triphenylphosphine (17.04 g, 0.065 mol) in 250 mL of dry THF was added dropwise diisopropyl azodicarboxylate (12.8 mL, 0.065 mol) and the resulting slurry was stirred at 0° C. for 1 h. To this mixture was added dropwise a solution of 4-hydroxymethyl-3-methylpyridine (4.0 g, 0.0325 mol) in 100 mL of dry THF, followed by freshly distilled thiolacetic acid (4.64 mL, 0.065 mol). The resulting mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h to give an orange solution. The solution was concentrated (rotary evaporator) and then diluted with petroleum ether. The resulting mixture was filtered and the filtrate was evaporated to give an orange oil. Chromatography (silica gel/hexane then 10%→50% ethyl acetate-hexane) of this oil gave 7.0 g of a oil which was distilled (Kugelrohr) to give the pure product (6.0 g, 100%) as a yellow oil, b.p. (air-bath temperature) 95°-100° C./0.1 torr: 1Hnmr (CDCl3) δ8.40, 7.20 (ABq, J=5Hz, 2H), 8.37 (s, 1H), 4.08 (s, CH2), 2.35 (s, CH3), 2.32 (s, CH3); ir (neat) 1695 cm-1.

Provenance & Evidence