반응 #64427

반응 방정식

1-bromo-5-benzyloxy pentane

t-butyl lithium

3-bromo-phenol

n-pentyl ether

3-(benzyloxypentyl)-phenol

n-pentyl ether

→

3-(5-hydroxypentyl)-phenol

n-pentyl ether

용매

ethanol

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGis then stirred an additional 24 hours
2. 2
   기타before being quenched with silica gel
3. 3
   기타After removing the solvent
4. 4
   기타the mixture is chromatographed over silica gel (1:1 hexane:ether)
5. 5
   기타to yield a crude mixture
6. 6
   여과After filtering through celite
7. 7
   농축concentrating

실험 절차

At a temperature of -78° C., 19.4 ml of t-butyl lithium (1.7M) is added to 4.0 gm of the above 3-bromo-phenol, n-pentyl ether in 50 mls tetrahydrofuran; and to this is added 3.3 ml of a freshly prepared solution of Li2CuCl3 (0.10M/THF). The mixture is stirred for 10 minutes, and then 4.35 grams of the 1-bromo-5-benzyloxy pentane are added. The reaction is allowed to warm slowly to ambient temperature over 12 hours and is then stirred an additional 24 hours before being quenched with silica gel. After removing the solvent, the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture containing 3-(benzyloxypentyl)-phenol, n-pentyl ether. A solution of 6.0 gm of this crude mixture in ethanol is hydrogenated over 5% Pd on carbon for 5 hours. After filtering through celite and concentrating, pure 3-(5-hydroxypentyl)-phenol, n-pentyl ether is obtained as a clear oil by HPLC chromatography.

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