Pyridine → Furan, 2,5-bis(chloromethyl)-

Temperature

-40 °C

To a stirred solution of furan-2,5-dimethanol (25 mg, 0.2 mol) and pyridine (38.4 g, 0.48 mol) in a dry chloroform (120 mL) was added dropwise a solution of thionyl chloride (52.4 g, 0.44 mol) in dry chloroform (80 mL) at -40° C. (Ar) for 1.5 h. After addition, the mixture was stirred at -40° C. for 0.5 h then warmed to 0° C. for 0.5 h. After quenching with ice water (300 mL), the organic phase was washed with 5% sodium hydroxide (10 mL), dried, then evaporated to give a light brown oil. The brownish oil was distilled under vacuum (80°-82° C., 0.5 mmHg) to give a colorless liquid which solidified at room temperature. Yield: 24 g (75%); M.P. 27°-28° C. (M.P. 27°-28° C., K. Yu. Noritskii, V. P. Volkoo, and Yu. K. Yuiey, Zhur. Obscher. Khim., 1961, 31, 538.)

1. additionAfter addition
2. temperaturethen warmed to 0° C. for 0.5 h
3. customAfter quenching with ice water (300 mL)
4. washthe organic phase was washed with 5% sodium hydroxide (10 mL)
5. customdried
6. customevaporated
7. customto give a light brown oil
8. distillationThe brownish oil was distilled under vacuum (80°-82° C., 0.5 mmHg)
9. customto give a colorless liquid which
10. customsolidified at room temperature

ORD record

ord-de62db2fd5ce4162abe622df712a1ba0

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05162473