Thionyl Chloride → HCID 86715371, compound

Referring to FIG. 16, a slurry of sodium 3-(propargyloxy)propyl sulfonate (5.0 g, 25.0 mmol, 1.0 equiv.) and thionyl chloride (25 mL, 344 mmol, 13.8 equiv.) was heated to 100° C. under N2 for three hours. The mixture was concentrated to a thick oil, diluted with 50 mL benzene, and concentrated again by rotavap to obtain a waxy solid. The material was slurried in 50 mL dichloromethane and filtered. The solids were discarded and the mother liquor concentrated on rotavap to obtain product as an orange oil (4.7 g, 95%). 1H NMR (300 MHz, CDCl3) δ 4.17 (d, 2H), 3.82 (t, 2H), 3.70 (t, 2H), 2.47 (t, 1H), 2.34 (m, 2H).

1. concentrationThe mixture was concentrated to a thick oil
2. additiondiluted with 50 mL benzene
3. concentrationconcentrated again by rotavap
4. customto obtain a waxy solid
5. filtrationfiltered
6. concentrationthe mother liquor concentrated on rotavap

ORD record

ord-314aaaf101b7448c8768125f1895d49f

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309283B2