Ethyl Propionate → HCID 67828441, compound

To a stirred solution of diisopropylamine (1.19 g, 11.9 mmol) in dry tetrahydrofuran (20 ml), at -40° C. under dry nitrogen was added a solution of n-butyllithium in hexane (2.5M; 4.76 ml, 11.9 mmol). The resulting solution was stirred for 0.5 hours, whilst being allowed to warm to room temperature, then cooled to -70° C. before dropwise addition of a solution of ethyl propanoate (1.19 ml, 10 mmol) in dry tetrahydrofuran (20 ml), at such a rate that the temperature did not exceed -65° C. After a further 10 minutes, a solution of N-(trimethylsilyl)cinnamaldimine [prepared by the addition of trans cinnamaldehyde (1.32 g, 10 mmol) to a solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M; 10 ml, 10 mmol) under dry nitrogen at room temperature] was added, again maintaining the internal temperature at <65° C., and stirring was continued for 15 minutes at -70° C. before removal of the cooling bath.

1. customdid not exceed -65° C
2. waitAfter a further 10 minutes
3. additionwas added
4. temperatureagain maintaining the internal temperature at <65° C.
5. stirringstirring
6. customwas continued for 15 minutes at -70° C. before removal of the cooling bath

ORD record

ord-091af0f40a4a410caf55eb8b67cc3d3a

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05362902