تفاعل #1572285

معادلة التفاعل

compound

trans-4-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylcyclohexanecarboxamide

triethylsilane

sodium hydrogencarbonate

Bismuth tribromide

4-fluorobenzaldehyde

→

titled compound

المردود 62.3%

trans-4-[(4-fluorobenzyl)oxy]-N-methoxy-N-methylcyclohexanecarboxamide

المردود 62.3%

المذيبات

acetonitrile

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder cooling with ice
2. 2
   أخرىthe insoluble matter was removed by filtration through Celite (registered trademark)
3. 3
   أخرىThe organic layer in the filtrate was separated
4. 4
   غسيلwashed with saturated brine
5. 5
   تجفيفThe washed organic layer was dried over anhydrous magnesium sulfate
6. 6
   أخرىafter removing the
7. 7
   ترشيحdesiccant by filtration
8. 8
   تركيزthe filtrate was concentrated under reduced pressure
9. 9
   أخرىThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-50:50)

الإجراء التجريبي

To a solution in acetonitrile (11 mL) of the compound (1.00 g) obtained in step (2) above, triethylsilane (579 mg) was added. Bismuth tribromide (104 mg) and 4-fluorobenzaldehyde (617 mg) were added under cooling with ice and the mixture was stirred at room temperature for two hours. To the reaction mixture, a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added and the insoluble matter was removed by filtration through Celite (registered trademark). The organic layer in the filtrate was separated and washed with saturated brine. The washed organic layer was dried over anhydrous magnesium sulfate and after removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-50:50) to give the titled compound as a colorless oil (0.61 g).

المصدر