Triphenylphosphine → HCID 13824169, compound

Temperature

0 °C

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.

1. stirringThe resulting mixture was stirred at 0° C. for 1 h
2. customat room temperature for 1 h to give an orange solution
3. concentrationThe solution was concentrated
4. custom(rotary evaporator)
5. additiondiluted with petroleum ether
6. filtrationThe resulting mixture was filtered
7. customthe filtrate was evaporated
8. customto give an orange oil

ORD record

ord-94258de624dd45fabd76ea95bb740b70

Source dataset

uspto-grants-1987_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04644061