Sodium Cyanide → 2-(Hydroxyimino)-3-methoxy-3-methylbutanenitrile

53.6 g (0.46 mol) of 2-methoxy-2-methylpropionaldehyde oxime in ether (about 1M) are initially taken at from −5° to −10° C. 35.8 g (0.5 mol) of chlorine gas are passed in, after which stirring is carried out for 1 hour at this temperature and the mixture is then evaporated down at 10° C. and the residue is taken up in diethyl ether. 24.7 g (0.5 mol) of sodium cyanide in 375 ml of 20:1 methanol/H2O are initially taken at 10° C. and the above ethereal solution is rapidly added dropwise. After 4 hours at room temperature, the mixture is filtered under suction and the residue is washed with twice 100 ml of methanol. The combined solutions are evaporated down and the residue is partitioned between methyl tert-butyl ether and water. Drying the organic phase over Na2SO4, evaporating down and crystallizing from dichloromethane/n-hexane give 41.1 g (63% of theory) of a white powder of melting point 102°-104° C.

1. customare initially taken at from −5° to −10° C
2. customthe mixture is then evaporated down at 10° C.
3. customare initially taken at 10° C.
4. additionthe above ethereal solution is rapidly added dropwise
5. waitAfter 4 hours at room temperature
6. filtrationthe mixture is filtered under suction
7. washthe residue is washed with twice 100 ml of methanol
8. customThe combined solutions are evaporated down
9. customthe residue is partitioned between methyl tert-butyl ether and water
10. dry with materialDrying the organic phase over Na2SO4
11. customevaporating down
12. customcrystallizing from dichloromethane/n-hexane
13. customgive 41.1 g (63% of theory) of a white powder of melting point 102°-104° C.

ORDレコード

ord-2f8274fff94a4912acaf55292ebc16a1

出典データセット

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

USRE037839E1