Реакция #44493

Уравнение реакции

NaH

but-2-ene-1,4-diol

tert-butyl-chlorodiphenylsilane

→

4-(tert-Butyl-diphenyl-silanyloxy)-but-2-en-1-ol

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGstirred for another two hours
3. 3
   workup.ADDITIONwas added drop wise
4. 4
   workup.WAITAfter twenty minutes
5. 5
   Другоеthe cooling bath was removed
6. 6
   workup.STIRRINGto stir overnight at room temperature
7. 7
   workup.ADDITIONSaturated NH4Cl was poured into the reaction mixture
8. 8
   Другоеthe reaction was partitioned with diethyl ether (200 mL)
9. 9
   ПромывкаThe organic layer was washed with brine
10. 10
    Сушкаdried (MgSO4)
11. 11
    Фильтрацияfiltered
12. 12
    ДругоеThe resulting oil was used in the following step without further purification

Методика

NaH (3 g, 75 mmol, 60% in oil) was added portion-wise to a stirred and cooled (0° C.) solution of but-2-ene-1,4-diol (6 g, 68.09 mmol) in dry tetrahydrofuran (250 mL). After the addition, the mixture was allowed to warm to room temperature and stirred for another two hours. The resulting white mixture was then cooled (0° C.) and tert-butyl-chlorodiphenylsilane (15.7 mL, 61.28 mmol) was added drop wise. After twenty minutes, the cooling bath was removed and the mixture was allowed to stir overnight at room temperature. Saturated NH4Cl was poured into the reaction mixture and the reaction was partitioned with diethyl ether (200 mL). The organic layer was washed with brine, dried (MgSO4), and filtered. The resulting oil was used in the following step without further purification.

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