反应详情

A suspension of 0.432 g. (11.36 mmoles) of lithium aluminum hydride in 20 ml. of anhydrous ether was stirred with ice bath cooling while a solution of 1.73 g. (5.68 mmoles) of rac. ethyl 8-benzyloxy-3,7-dimethyl-4-octenoate in 20 ml. of anhydrous ether was added over a 25 minute period keeping the temperature at 0°-5° C. The cooling bath was removed and the reaction mixture was stirred at room temperature for 2.5 hours at the end of which time 1.6 ml. of saturated sodium sulfate solution was cautiously added with ice bath cooling. After stirring for 16 hours at room temperature, the slurry was filtered on Celite and the filter cake was washed thoroughly with ether. Concentration in vacuo of the combined filtrate and washes yielded 1.46 g. of a colorless oil. This material was chromatographed in 50 g. of silica gel. Elution with 2:1 parts by volume, 1:1 parts by volume and 1:2 parts by volume hexane-ether afforded 1.38 g. of rac. E-8-benzyloxy-3,7-dimethyl-4-octen-1-ol which was evaporatively distilled giving 1.37 g. (92%) of colorless oil, b.p. 107°-108° C. (bath temperature) (0.03 mm Hg.).

1. additionA suspension of 0.432 g
2. temperaturecooling while a solution of 1.73 g
3. customat 0°-5° C
4. customThe cooling bath was removed
5. additionof saturated sodium sulfate solution was cautiously added with ice bath
6. temperaturecooling
7. stirringAfter stirring for 16 hours at room temperature
8. filtrationthe slurry was filtered on Celite
9. washthe filter cake was washed thoroughly with ether
10. concentrationConcentration in vacuo of the combined filtrate and washes
11. customyielded 1.46 g
12. customThis material was chromatographed in 50 g
13. washElution with 2:1 parts by volume, 1:1 parts by volume and 1:2 parts by volume hexane-ether
14. customafforded 1.38 g
15. distillationof rac. E-8-benzyloxy-3,7-dimethyl-4-octen-1-ol which was evaporatively distilled
16. customgiving 1.37 g