Reaktion #319066

Reaktionsgleichung

(4-phenylbutyl)-phosphinic acid, ethyl ester

trimethylsilyl chloride

triethylamine

acrylate

triethylamine

→

title compound

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

Lösungsmittel

ethyl acetate

chloroform

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

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