تفاعل #674306

معادلة التفاعل

Ether

Ethyl chloroformate

4-(benzyloxy)cyclohexanecarbonitrile

LDA

→

ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate

المردود 33.6%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe solution was stirred at −78° C.
2. 2
   درجة الحرارةto warm to room temperature slowly
3. 3
   workup.STIRRINGstirred overnight
4. 4
   أخرىThe reaction was quenched by addition of H2O (20 mL), HCl (1.0 N, 20 mL)
5. 5
   استخلاصIt was then extracted with EtOAc (3×40 mL)
6. 6
   غسيلThe combined organic solution was washed with brine (50 mL)
7. 7
   تجفيفdried over anhydrous Na2SO4
8. 8
   تركيزconcentrated
9. 9
   أخرىto give pale yellow residue
10. 10
    workup.STIRRINGstirred for 5 min
11. 11
    ترشيحfiltered
12. 12
    أخرىto remove the white solid
13. 13
    تركيزThe ethereal solution was concentrated
14. 14
    أخرىto give the yellow oil which
15. 15
    أخرىwas purified by CombiFlash (25 g silica gel column, EtOAc/Hexane: 0-20%)

الإجراء التجريبي

To a solution of 4-(benzyloxy)cyclohexanecarbonitrile (1.26 g, 5.85 mmol, 1.0 equiv) in THF (dry, 30 mL) was added a solution of LDA (3.95 mL, 2.0 M Heptane/THF/toluene, 1.35 equiv) dropwise at −78° C. under N2. The resulting yellow solution was stirred at −78° C. for 2 hrs. Ethyl chloroformate (2.79 mL, 29.26 mmol, 5.0 equiv) was then added by syringe dropwise. The solution was stirred at −78° C. and allowed to warm to room temperature slowly and stirred overnight. The reaction was quenched by addition of H2O (20 mL), HCl (1.0 N, 20 mL). It was then extracted with EtOAc (3×40 mL). The combined organic solution was washed with brine (50 mL), dried over anhydrous Na2SO4 and then concentrated to give pale yellow residue. Ether (40 mL) was added and stirred for 5 min, filtered to remove the white solid. The ethereal solution was concentrated to give the yellow oil which was purified by CombiFlash (25 g silica gel column, EtOAc/Hexane: 0-20%) to afford 565 mg (yield 33%) of ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate as a pale yellow oil.

المصدر