Reaktion #95966

Reaktionsgleichung

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

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas placed in a refrigerator overnight
2. 2
   SonstigeUpon removal from the refrigerator
3. 3
   Sonstigethe bulk of the solvent was removed on a rotary evaporator
4. 4
   ExtraktionThe separated aqueous layer was extracted with diethyl ether
5. 5
   Sonstigedried
6. 6
   Sonstigeto yield the crude
7. 7
   SonstigeRecrystallization
8. 8
   workup.ADDITIONfrom a mixture of methylene chloride and Skellysolve® B
9. 9
   Sonstigegave product

Vorschrift

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:

Quelle