반응 #319066

반응 방정식

(4-phenylbutyl)-phosphinic acid, ethyl ester

trimethylsilyl chloride

triethylamine

acrylate

triethylamine

→

title compound

(E)-3-[Ethoxy(4-phenylbutyl)phosphinyl]-2-propenoic acid, methyl ester

용매

ethyl acetate

chloroform

반응 조건

후처리

1. 1
   농축after which it was concentrated in vacuo
2. 2
   workup.STIRRINGThe resulting yellow mixture was stirred overnight at 65° C.
3. 3
   기타resulting in an orange semisolid
4. 4
   세척washed sequentially with 1N hydrochloric acid and saturated sodium bicarbonate solution
5. 5
   건조dried (MgSO4)
6. 6
   농축concentrated to an orange oil
7. 7
   세척eluting with a gradient from 1:1 hexane

실험 절차

A solution of (4-phenylbutyl)-phosphinic acid, ethyl ester (8.0 g, 35.4 mmols) in chloroform (40 ml) were added trimethylsilyl chloride (13.5 ml, 106 mmols) and triethylamine (19.7 ml, 142 mmols). The resulting mixture was stirred at 25° C. for 2.5 hours, after which it was concentrated in vacuo. To the residue were added methyl α-chloro=acrylate (20 g, 0.16 mole, prepared as described by C. S. Marvel and J. C. Cowan, J. Amer. Chem. Soc. 61, 3156 (1939)) and triethylamine (9.0 ml, 64 mmol). The resulting yellow mixture was stirred overnight at 65° C., resulting in an orange semisolid. The mixture was diluted with ethyl acetate and washed sequentially with 1N hydrochloric acid and saturated sodium bicarbonate solution, dried (MgSO4), and concentrated to an orange oil. The oil was chromotographed on LPS-1 silica gel, eluting with a gradient from 1:1 hexane:ethyl acetate to ethyl acetate, to give the title compound.

출처