반응 #70828

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

cyclopent-3-enecarboxylic acid

→

2-phenylpropan-2-yl cyclopent-3-enecarboxylate

수율 90.4%

용매

cyclohexane

methylene chloride

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후처리

1. 1
   기타precipitated
2. 2
   여과The precipitate was collected by filtration
3. 3
   세척rinsed with hexanes
4. 4
   농축The combined filtrates were concentrated in vacuo
5. 5
   기타to yield a residue
6. 6
   기타The residue was purified over a 330 g silica gel column
7. 7
   세척eluting at 100 mL/min with a 0-5% ethyl acetate/hexanes

실험 절차

A solution of 2-phenylpropan-2-yl 2,2,2-trichloroacetimidate (23.85 g, 85 mmol) in cyclohexane (85 mL) was treated with a solution of cyclopent-3-enecarboxylic acid (4.77 g, 42.5 mmol) in methylene chloride (43 mL), and the mixture was stirred for about 16 hours at room temperature during which time a colorless solid precipitated. The precipitate was collected by filtration and rinsed with hexanes. The combined filtrates were concentrated in vacuo to yield a residue. The residue was purified over a 330 g silica gel column, eluting at 100 mL/min with a 0-5% ethyl acetate/hexanes gradient over 2 column volumes, then 5% ethyl acetate/hexanes for 2 column volumes, then a 5-40% ethyl acetate/hexanes gradient over 10 column volumes to yield 2-phenylpropan-2-yl cyclopent-3-enecarboxylate (8.84 g, 38.4 mmol, 90% yield) as a yellow oil.

출처