Ethyl cyanoacetate → Ethyl 4-cyanooxane-4-carboxylate

Temperature

100 °C

Ethyl cyanoacetate (22.6 g, 0.2 mol) and bis(2-chloroethyl)ether (14 g, 0.1 mol) were added to a suspension of potassium carbonate (70 g, 0.5 mol) in N,N-dimethylformamide (150 ml), and the mixture stirred at 100° C. for 72 hours. The cooled mixture was partitioned between water and diethyl ether (500 ml), the layers separated and the aqueous solution extracted with diethyl ether (3×200 ml). The combined organic solutions were washed with 2N hydrochloric acid (3×100 ml), brine (2×100 ml), dried (MgSO4) and evaporated under reduced pressure to give a yellow oil. This crude product was purified by column chromatography on silica gel using ethyl acetate:cyclohexane (50:50) as eluant, to afford the title compound, 9.3 g.

1. customThe cooled mixture was partitioned between water and diethyl ether (500 ml)
2. customthe layers separated
3. extractionthe aqueous solution extracted with diethyl ether (3×200 ml)
4. washThe combined organic solutions were washed with 2N hydrochloric acid (3×100 ml), brine (2×100 ml)
5. dry with materialdried (MgSO4)
6. customevaporated under reduced pressure
7. customto give a yellow oil
8. customThis crude product was purified by column chromatography on silica gel

ORD record

ord-1eeacd3348ac4d499bd63df88a2ad544

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060836B2