تفاعل #74380

معادلة التفاعل

(1R,2S,4R,5S)-bicyclo[2.2.1]-heptane-2,5-diol

15-crown-5

tetrahydrofuran

sodium hydroxide

1-(bromomethyl)benzene

→

title compound

(1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-ol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred at ambient temperature overnight
2. 2
   أخرىThe mixture was partitioned between EtOAc and water
3. 3
   غسيلthe organic portions were washed with brine
4. 4
   أخرىThe crude product was purified by flash column chromatography (0 to 80% of ethyl acetate in hexanes)

الإجراء التجريبي

To a stirred solution of (1R,2S,4R,5S)-bicyclo[2.2.1]-heptane-2,5-diol (1.15 g, 8.97 mmol) and 15-crown-5 (0.054 mL, 0.269 mmol) in tetrahydrofuran (30.0 mL, 8.97 mmol) were added at 10° C. (ice/water bath) finely ground sodium hydroxide (2.15 g, 53.8 mmol) and 1-(bromomethyl)benzene (1.07 mL, 8.97 mmol). After stirring at 10° C. for 3 h, the mixture was stirred at ambient temperature overnight. The mixture was partitioned between EtOAc and water, and the organic portions were washed with brine, and conc. in vacuo. The crude product was purified by flash column chromatography (0 to 80% of ethyl acetate in hexanes). The title compound was obtained as a colorless oil.

المصدر