反応 #312592

反応方程式

1,2,6-trihydroxyhexane

benzaldehyde dimethylacetal

→

title product

収率 66.3%

4-[(2-Phenyl)-1,3-dioxolan-4-yl]-1-butanol

収率 66.3%

溶媒

DMF

ethyl acetate

反応条件

後処理

1. 1
   温度cooled
2. 2
   ろ過filtered
3. 3
   濃縮The filtrate was concentrated
4. 4
   その他residue obtained
5. 5
   洗浄After being washed with water and brine
6. 6
   乾燥the solution was dried over Na2SO4
7. 7
   その他The crude product obtained
8. 8
   その他after evaporation of the solvent
9. 9
   その他was chromatographed on silica eluting with ethyl acetate

実験手順

To a solution of 1,2,6-trihydroxyhexane (10.0 g, 74.6 mmol) and benzaldehyde dimethylacetal (15.0 g, 98.7 mmol) in dry DMF (10 mL) was added Amberlyst 15 (5.0 g). The mixture was stirred at 100° C. for 5 min, then cooled and filtered. The filtrate was concentrated and residue obtained was re-dissolved in ethyl acetate. After being washed with water and brine, the solution was dried over Na2SO4. The crude product obtained after evaporation of the solvent was chromatographed on silica eluting with ethyl acetate. Concentration of the proper fractions afforded 11.0 g (66%) of the title product (a mixture of diastereomers) as a colorless oil: 1H NMR (CDCl3, 300 MHz, ppm) 7.48 (m, 2H), 7.39 (m, 3H), 5.92 (s, 0.4H), 5.80 (s, 0.6H), 4.3-4.1 (m, 2H), 3.64 (m, 3H), 1.8-1.4 (m, 6H).

出典