反应 #6609

反应方程式

ethyl chloroformate

4-carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

triethylamine

sodium borohydride

hydrochloric acid

→

title compound

收率 37.7%

4-Hydroxymethylbenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

收率 37.7%

溶剂

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

water

反应条件

后处理

1. 1
   过滤the solid was filtered off
2. 2
   workup.WAITto reach room temperature within 1 h
3. 3
   其他Most of the tetrahydrofuran was removed in a rotary evaporator
4. 4
   萃取the remaining aqueous phase was extracted with chloroform
5. 5
   干燥The organic phase was dried over Na2SO4
6. 6
   浓缩concentrated
7. 7
   其他Fractional crystallization from ethyl acetate

实验过程

A solution of 0.97 g (9 mmol) of ethyl chloroformate in 5 ml of tetrahydrofuran was added dropwise to a solution of 3 g (9 mmol) of 4-carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether and 0.9 g (9 mmol) of triethylamine in 20 ml of dry tetrahydrofuran at 0° C. The mixture was stirred at 0° C for 30 min, the solid was filtered off, and the filtrate was added dropwise to a solution of 0.83 g (22 mmol) of sodium borohydride in 8 ml of tetrahydrofuran and 8 ml of water. The reaction mixture was then allowed to reach room temperature within 1 h and was then acidified with 1N hydrochloric acid. Most of the tetrahydrofuran was removed in a rotary evaporator, and the remaining aqueous phase was extracted with chloroform. The organic phase was dried over Na2SO4 and concentrated. Fractional crystallization from ethyl acetate, discarding the first fraction, resulted in 1.1 g of the title compound of melting point 108°-109° C.

来源