Hydrochloric Acid → Diniconazole

온도

-73 °C

A chiral metal-hydrogen complex was formed in a manner similar to that in Example 1 by adding to 20 cc of an ethyl ether solution containing 0.63 g of LiAlH4 50 cc of an ethyl ether solution containing 3.05 g of N-methylephedrine followed by 20 cc of an ethyl ether solution containing 4.12 g of N-ethylaniline. To the resulting solution, was added at -70° C. 30 cc of an ethyl ether solution containing 1.62 g of (E)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one. The resulting mixture was stirred at -73° C. for 5 hours under adiabatic conditions and left standing overnight at room temperature. To the mixture was added 60 cc of 2 N hydrochloric acid to effect decomposition. The organic layer was washed successively with 100 cc of a saturated sodium hydrogencarbonate solution and 100 cc of ice-cooled water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 1.82 g of crude crystals. The crude crystals were recrystallized three times from a cyclohexane-methanol mixture to obtain 0.41 g of (+)-(E)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol: [α]D24 +29.2 (c=1.0, CHCl3); melting point 160°-161° C. The NMR spectrum was identical with that of the racemate described in Reference Example 2.

1. customA chiral metal-hydrogen complex was formed in a manner similar to that in Example 1
2. additionTo the resulting solution, was added at -70° C
3. waitleft
4. waitstanding overnight at room temperature
5. washThe organic layer was washed successively with 100 cc of a saturated sodium hydrogencarbonate solution and 100 cc of ice-
6. temperaturecooled water
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customto obtain 1.82 g of crude crystals
10. customThe crude crystals were recrystallized three times from a cyclohexane-methanol mixture

ORD 기록

ord-e5bb3aa76ee946e7916d5f277304484a

출처 데이터셋

uspto-grants-1984_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04435203