Реакция #94736

Уравнение реакции

LiAlH4

LiAlH4

Na2SO4

ethyl 5-(4-methoxyphenyl)-3,3-ethylenedioxypentanoate

→

3,3-Ethylenedioxy-5-(4-methoxyphenyl)-1-pentanol

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеflask equipped with mechanical stirrer
2. 2
   Температураreflux condenser
3. 3
   Температураheating mantle
4. 4
   workup.ADDITIONwas added 18 g
5. 5
   Температураrefluxed for 2 hrs
6. 6
   ФильтрацияThe inorganic solid was filtered off
7. 7
   Промывкаwashed with ethyl acetate
8. 8
   КонцентрированиеThe filtrate was concentrated in vacuo
9. 9
   Другоеleaving 84.6 g

Методика

Into a 2 l. 3-necked r.b. flask equipped with mechanical stirrer, reflux condenser, and heating mantle was added 18 g. (0.474 mole) of LiAlH4 and 500 ml. of dry tetrahydrofuran at such a rate as to control vigorous reflux of reaction solution. 97 g. (0.33 mole) of ethyl 5-(4-methoxyphenyl)-3,3-ethylenedioxypentanoate in 100 ml. of dry tetrahydrofuran and added dropwise over a period of 40 minutes. The reaction mixture was stirred at room temperature for 30 minutes and refluxed for 2 hrs. Excess LiAlH4 was carefully decomposed with saturated Na2SO4 solution. The inorganic solid was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo leaving 84.6 g. of crude ketal alcohol.

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