반응 #95966

반응 방정식

p-trifluoromethylbenzoyl chloride

ketal

3,4-Dichloro-N-[(8-(dimethylamino)-1,4-dioxaspiro[4.5]dec-8-yl)methyl]benzamide

triethylamine

→

α,α,α-trifluoro-N-[[8-(dimethylamino)-1,4-dioxaspiro[4.5]dec-8-yl]methyl]-p-toluamide

용매

THF

THF

반응 조건

후처리

1. 1
   기타was placed in a refrigerator overnight
2. 2
   기타Upon removal from the refrigerator
3. 3
   기타the bulk of the solvent was removed on a rotary evaporator
4. 4
   추출The separated aqueous layer was extracted with diethyl ether
5. 5
   기타dried
6. 6
   기타to yield the crude
7. 7
   기타Recrystallization
8. 8
   workup.ADDITIONfrom a mixture of methylene chloride and Skellysolve® B
9. 9
   기타gave product

실험 절차

A solution of 1.0 g (0.00465 mole) of the ketal from Example 1, part A and 0.47 g (0.65 ml) of triethylamine in 15 ml of THF was cooled in an ice bath. To this cooled solution there was added a solution of 0.97 g (0.00465 mole) of p-trifluoromethylbenzoyl chloride in 10 ml of THF over 10 minutes while stirring. The mixture was placed in a refrigerator overnight. Upon removal from the refrigerator, the bulk of the solvent was removed on a rotary evaporator. The residue was taken up in diethyl ether and aqueous sodium bicarbonate solution. The separated aqueous layer was extracted with diethyl ether. The diethyl ether liquid fractions were pooled and dried to yield the crude, named product, 2.07 g, m.p. 128°-130° C. Recrystallization from a mixture of methylene chloride and Skellysolve® B gave product weighing 1.56 g, m.p. 129°-130.5° C. The elemental analysis was as follows:

출처