Diethyl chlorophosphate → HCID 131730025, compound

Temperature

0 °C

29 (rac-Ethyl (2E)-4-hydroxy-2-methylpent-2-enoate) (0.99 g, 6.0 mmol) is dissolved in pyridine (1.6 ml) and cooled to 0° C. Diethylchlorophosphate (1.1 ml, 7.5 mmol) is added under stirring over 20 min at ≧3° C. After 4.5 hours of additional stirring at 0° C., the reaction mixture is quenched with 1 M H2SO4 (100 ml) and extracted with tBuOMe (300 ml) successively. The organic phase is washed with brine (50 ml), saturated NaHCO3 (50 ml) and brine (50 ml). The organic phase is dried with Na2SO4 and evaporated under reduced pressure at 40° C. The residue is purified by flash chromatography (AcOiPr:heptane fraction 50:50 to 60:40) to yield 17 (rac-Ethyl (2E)-4-(diethoxyphosphinyloxy)-2-methylpent-2-enoate) (1.56 g, 88%) as a yellowish oil.

1. stirringAfter 4.5 hours of additional stirring at 0° C.
2. customthe reaction mixture is quenched with 1 M H2SO4 (100 ml)
3. extractionextracted with tBuOMe (300 ml) successively
4. washThe organic phase is washed with brine (50 ml), saturated NaHCO3 (50 ml) and brine (50 ml)
5. dry with materialThe organic phase is dried with Na2SO4
6. customevaporated under reduced pressure at 40° C
7. customThe residue is purified by flash chromatography (AcOiPr:heptane fraction 50:50 to 60:40)

ORD record

ord-06293888e3bd4494a08e7a710c7ee05a

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288566B2