Chlorotrimethylsilane → HCID 13359882, compound

Temperature

0 °C

To a solution of 4-phenylbutyl phosphonous acid, ethyl ester (0.5 g, 0.0022 mole) in chloroform (10 ml) was added triethylamine (0.34 ml, 0.0024 mole) and the solution was cooled in an ice bath to 0° C. Trimethyl silyl chloride (0.31 ml, 0.0024 mole) was added to the above solution dropwise, followed by ethyl bromoacetate (0.27 ml, 0.0024 mole). The ice bath was removed and the mixture stirred at room temperature for 6 hours and poured into 50% aqueous HCl (30 ml) and crushed ice (20 g). After shaking the mixture in a separatory funnel, the chloroform layer was separated and the aqueous layer extracted with dichloromethane (2×50 ml). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and the solvents removed on a rotavap. The resulting yellow oil (0.6 g) was vacuum dried to get 0.58 (84%) of title compound. TLC, silica gel, acetone:hexane (1:1), Rf =0.28.

1. customThe ice bath was removed
2. additionpoured into 50% aqueous HCl (30 ml)
3. customcrushed ice (20 g)
4. stirringAfter shaking the mixture in a separatory funnel
5. customthe chloroform layer was separated
6. extractionthe aqueous layer extracted with dichloromethane (2×50 ml)
7. washThe combined organic phase was washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. customthe solvents removed on a rotavap
10. customdried

ORD record

ord-d02b42002b4c4440a8821b76ee492632

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04602092