反応 #95966

反応方程式

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

溶媒

THF

THF

反応条件

後処理

1. 1
   その他was placed in a refrigerator overnight
2. 2
   その他Upon removal from the refrigerator
3. 3
   その他the bulk of the solvent was removed on a rotary evaporator
4. 4
   抽出The separated aqueous layer was extracted with diethyl ether
5. 5
   その他dried
6. 6
   その他to yield the crude
7. 7
   その他Recrystallization
8. 8
   workup.ADDITIONfrom a mixture of methylene chloride and Skellysolve® B
9. 9
   その他gave product

実験手順

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:

出典