Реакция #1515069

Уравнение реакции

4-(adamantan-1-ylmethoxy)-3-(1-hydroxycyclobutyl)-benzonitrile

triethylsilane

trifluoroacetic acid

→

4-(adamantan-1-ylmethoxy)-3-cyclobutylbenzonitrile

Растворители

methylene chloride

sodium hydroxide

Условия реакции

Обработка

1. 1
   ЭкстракцияThe mixture was extracted with methylene chloride (3×50 mL)
2. 2
   ПромывкаThe combined organic layers were washed with brine (50 mL)
3. 3
   Сушкаdried over anhydrous magnesium sulfate
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеThe residue was purified by column chromatography
7. 7
   Промывкаeluting with a 5% to 10% gradient of ethyl acetate in hexanes

Методика

To a cooled (0° C.) stirred solution of 4-(adamantan-1-ylmethoxy)-3-(1-hydroxycyclobutyl)-benzonitrile (1.00 g, 2.96 mmol) in methylene chloride (30 mL) was added triethylsilane (2.4 mL, 14.80 mmol) followed by trifluoroacetic acid (2.3 mL, 29.60 mmol). The reaction mixture was stirred at 0° C. for 1.5 h and diluted with 1M aqueous sodium hydroxide solution (30 mL). The mixture was extracted with methylene chloride (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 5% to 10% gradient of ethyl acetate in hexanes to afford 4-(adamantan-1-ylmethoxy)-3-cyclobutylbenzonitrile as colorless solid in quantitative yield (0.95 g): MS (ES+) m/z 322.2 (M+1);

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