تفاعل #70827

معادلة التفاعل

trichloroacetonitrile

sodium hydride

2-phenylpropan-2-ol

methanol

→

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

المردود 103.7%

المذيبات

—

hexanes

diethyl ether

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   درجة الحرارةto warm to room temperature over 1 hour
3. 3
   تركيزwas concentrated in vacuo
4. 4
   أخرىto yield a residue
5. 5
   workup.STIRRINGthe resulting mixture was stirred vigorously for 5 minutes
6. 6
   ترشيحThe resulting black suspension was filtered through glass fiberglass
7. 7
   ترشيحfilter paper
8. 8
   غسيلthe collected solids were rinsed 3× with hexanes
9. 9
   تركيزThe combined filtrates were concentrated in vacuo

الإجراء التجريبي

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.

المصدر