Tetrahydrofuran → 2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

7.9 g (50 mmol) of 2,2-difluoro-1,3-benzodioxole are metallated according to Example 2 at -15° C. with 35 ml (55 mmol) of n-butyllithium (1.60M in hexane) and 6.5 g (55 mmol) of TMEDA in 60 ml of hexane. To the 2,2-difluoro-1,3-benzodioxol-4-yllithium which precipitates there is added at -20° C., over a period of 30 minutes, a solution of 9.3 g (55 mmol) of ethoxymethylenecyanoacetic acid ethyl ester in 30 ml of tetrahydrofuran, an orange-red turbid solution being formed during the reaction, which is exothermic. After stirring for 20 minutes at -15° C., the solution is hydrolysed with 50 ml of 2N hydrochloric acid. The aqueous phase is extracted twice with 80 ml of diethyl ether each time. The organic solutions are washed twice with 50 ml of water each time, dried over MgSO4 and concentrated to dryness by evaporation in a vacuum rotary evaporator. The residue is crystallised from ethanol/water 4:1, affording 10.1 g (72%) of colourless platelets of m.p. 87°-88° C.

1. customTo the 2,2-difluoro-1,3-benzodioxol-4-yllithium which precipitates there
2. additionis added at -20° C., over a period of 30 minutes

ORDレコード

ord-96035804ea854177a51b33bb4396b8b9

出典データセット

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05420301