Diethyl Ether → [Ethoxy(4-phenylbutyl)phosphoryl]acetic acid

Temperatur

0 °C

To a solution of 4-phenylbutyl phosphonous acid, ethyl ether (0.5 g, 0.0022 mole) in chloroform (10 ml) was added triethylamine (0.68 ml, 0.0048 mole) and the solution was cooled in an ice bath to 0° C. Trimethyl silyl chloride (0.6 ml, 0.0048 mole) was added to the above solution dropwise, followed by bromoacetic acid (0.34 g, 0.0024 mole). The ice bath was removed and the mixture stirred at room temperature for 5 hours and poured into 10% 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 crude thick oil was vacuum dried to get 0.61 g (97%) of title compound in the form of an oil, TLC: Silica gel, CH2Cl2 :MeOH:HOAc shows one main spot at Rf =0.37.

1. customThe ice bath was removed
2. additionpoured into 10% 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-Eintrag

ord-1f460e3036be4135ae4478e6628ba798

Quelldatensatz

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04602092