Chlorotrimethylsilane → [Hydroxy-(4-phenylbutyl)phosphinyl]acetic acid, ethyl ester

Temperatur

0 °C

To a solution of 4-phenylbutyl phosphonous acid (1.0 g, 0.005 mole) in chloroform (20 ml) was added triethylamine (1.6 ml, 0.011 mole) and the solution was cooled in an ice bath to 0° C. Trimethyl silyl chloride (1.4 ml, 0.011 mole) was added to the above solution dropwise, followed by ethyl bromoacetate (0.84 g, 0.56 ml, 0.011 mole). The ice bath was removed and the mixture stirred at room temperature overnight. The mixture was poured into 10% aqueous HCl (10 ml) and crushed ice HCl (10 ml) and crushed ice (10 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 crude thick oil (1.42 g) was vacuum dried to get 1.42 g (99%) of title compound in the form of an oil. TLC: silica gel, CH2Cl2 :MeOH:HOAc shows one main spot, but elongated, Rf =0.29.

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

ORD-Eintrag

ord-d53e219db97841eab7ac8ba22da18f43

Quelldatensatz

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04602092