반응 #70827

반응 방정식

trichloroacetonitrile

sodium hydride

2-phenylpropan-2-ol

methanol

→

2-phenylpropan-2-yl 2,2,2-trichloroacetimidate

수율 103.7%

용매

—

hexanes

diethyl ether

diethyl ether

반응 조건

후처리

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   온도to warm to room temperature over 1 hour
3. 3
   농축was concentrated in vacuo
4. 4
   기타to yield a residue
5. 5
   workup.STIRRINGthe resulting mixture was stirred vigorously for 5 minutes
6. 6
   여과The resulting black suspension was filtered through glass fiberglass
7. 7
   여과filter paper
8. 8
   세척the collected solids were rinsed 3× with hexanes
9. 9
   농축The combined filtrates were concentrated in vacuo

실험 절차

A suspension of 60% sodium hydride in mineral oil (0.42 g, 10.50 mmol) in diethyl ether (10 mL) was treated with the dropwise addition of a solution of 2-phenylpropan-2-ol (12.02 mL, 86 mmol) in diethyl ether (30 mL). Upon completion of addition, the mixture was stirred for 30 minutes, during which time a nearly clear solution was observed. After this time, the mixture was cooled to 0° C. and then treated with the dropwise addition of trichloroacetonitrile (8.18 mL, 82 mmol), which caused the mixture to turn dark brown. The reaction was allowed to warm to room temperature over 1 hour, and then was concentrated in vacuo to yield a residue. The residue was dissolved in hexanes (10 mL) and treated with methanol (0.424 mL, 10.48 mmol), and the resulting mixture was stirred vigorously for 5 minutes. The resulting black suspension was filtered through glass fiberglass filter paper, and the collected solids were rinsed 3× with hexanes. The combined filtrates were concentrated in vacuo to yield 2-phenylpropan-2-yl 2,2,2-trichloroacetimidate (23.8 g, 85 mmol, 99% yield) as an amber oil which was used as-is in the next step.

출처