Tetrahydrofuran → HCID 86648104, compound

Temperature

-78 °C

0.81 ml of triethylamine (5.8 mmol) were precharged in 10 ml of abs. THF, and 0.76 g of 2-hydroxyvinyl carbamate (5.8 mmol) were added. The reaction solution was then cooled to −78° C., and 0.83 ml of diethylchlorophosphonite (5.8 mmol) in 4 ml of THF were added dropwise. After completion of the addition, the reaction mixture was stirred for 12 hours at room temperature. A white solid was filtered off, and the residue was washed with a 5% aqueous solution of sodium hydrogen carbonate (3×10 ml). The organic phase was then dried over sodium sulfate. After filtering off the siccative, the solvent was removed on a rotary evaporator. The crude product was purified by column chromatography on silica gel (PE:EE=1:5). 0.39 g (25% of th.) of the title compound were obtained as a colorless oil.

1. additionAfter completion of the addition
2. filtrationA white solid was filtered off
3. washthe residue was washed with a 5% aqueous solution of sodium hydrogen carbonate (3×10 ml)
4. dry with materialThe organic phase was then dried over sodium sulfate
5. filtrationAfter filtering off the siccative, the solvent
6. customwas removed on a rotary evaporator
7. customThe crude product was purified by column chromatography on silica gel (PE:EE=1:5)

ORD record

ord-49b225158520463ba7cc853d61458f6c

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999323B2