Реакция #2028883

Уравнение реакции

ethyl trifluoroacetate

1-tetralone

sodium methoxide

methanol

→

compound

Выход 81.0%

2-trifluoroacetyl-1-tetralone

Выход 81.0%

Растворители

HCl

ether

ether

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 14 hours
2. 2
   ДругоеThe phases were separated
3. 3
   Промывкаthe organic layer was washed with 3N HCl
4. 4
   Сушкаwith brine, dried over anhydrous MgSO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   Другоеformed which
8. 8
   Другоеwere isolated by filtration and air
9. 9
   Другоеdried

Методика

A 250 mL one necked round bottom flask equipped with a reflux condenser, nitrogen inlet and provisions for magnetic stirring was charged with ethyl trifluoroacetate (28.4 g, 0.2 mol) and 75 mL of ether. To this solution was added 48 mL of 25% sodium methoxide in methanol (0.21 mol). A solution of 1-tetralone (29.2 g, 0.2 mol) in 50 mL of ether was added over about 5 minutes. The reaction mixture was stirred at room temperature for 14 hours and was diluted with 100 mL of 3N HCl. The phases were separated and the organic layer was washed with 3N HCl, and with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was taken up in 70 mL of boiling ethanol/water and cooled to room temperature, whereupon crystals of 2-trifluoroacetyl-1-tetralone formed which were isolated by filtration and air dried to give pure compound (32 g, 81%): mp 48°-49° C.; 1H NMR CDCl3 δ 2.8 (m, 2H), 2.9 (m, 2H), 7.2 (d, j=3.0 Hz, 1H), 7.36 (m, 1H), 7.50 (m, 1H), 7.98 (m, 1H), 19F NMR CDCl3 δ −72.0. EI GC-MS M+=242.

Источник