反応 #675122

反応方程式

tert-butyl 4-hydroxyphenethylcarbamate

potassium carbonate

benzyl bromide

→

tert-butyl 4-(benzyloxy)phenethylcarbamate

溶媒

DMF

water

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate (3×75 mL)
2. 2
   洗浄washed with 100 mL of 1 N HCl
3. 3
   乾燥dried (Na2SO4)
4. 4
   その他evaporated
5. 5
   その他The residue was purified by flash chromatography on silica gel eluting with a mixture of hexane and ethyl acetate

実験手順

To a solution of 1.11 g (4.70 mmol) of tert-butyl 4-hydroxyphenethylcarbamate in 20 mL of DMF at 22° C. was added 1.3 g (9.4 mmol) of potassium carbonate and 0.700 mL (5.87 mmol) of benzyl bromide. The mixture was stirred for about 16 h at 22° C., diluted with 100 mL of water and extracted with ethyl acetate (3×75 mL). The organic layers were combined, washed with 100 mL of 1 N HCl, dried (Na2SO4), and evaporated. The residue was purified by flash chromatography on silica gel eluting with a mixture of hexane and ethyl acetate to give tert-butyl 4-(benzyloxy)phenethylcarbamate as an oil which later solidified under vacuum. Transformation of tert-butyl 4-(benzyloxy)phenethylcarbamate to tert-butyl 4-(benzyloxy)phenethyl(methyl)carbamate was accomplished in a manner analogous to Method B Step 1.

出典