반응 #533582

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N,N-dimethylformamide

(3-bromo-2-methylphenethoxy)(tert-butyl)dimethylsilane

(3-Bromo-2-methylphenethoxy)(tert-butyl)dimethylsilane

Intermediate 22

(3-Bromo-2-methylphenethoxy)(tert-butyl)dimethylsilane

butyllithium

→

titled compound

3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-methylbenzaldehyde

용매

THF

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후처리

1. 1
   workup.ADDITIONadded dropwise over 3 minutes
2. 2
   workup.ADDITIONadded dropwise over 2 minutes
3. 3
   기타to give a colourless solution
4. 4
   workup.STIRRINGstirred at −78° C. for a further 30 minutes
5. 5
   기타removed from the cooling bath
6. 6
   온도to warm to room temperature over 45 minutes
7. 7
   기타The solution was quenched by the addition of 10% aqueous ammonium chloride (100 mL)
8. 8
   추출the resulting mixture was extracted twice with diethyl ether
9. 9
   세척The combined organic phases were washed with brine
10. 10
    건조dried over anhydrous magnesium sulphate
11. 11
    농축concentrated in vacuo

실험 절차

A colourless solution of (3-bromo-2-methylphenethoxy)(tert-butyl)dimethylsilane [Aromatic Intermediate 22, step c] (2.06 g) in THF (40 mL) was cooled to −78° C. under an atmosphere of nitrogen and treated with butyllithium (2.1M in hexanes, 3.3 mL), added dropwise over 3 minutes. The resulting pale yellow solution was stirred at −78° C. for 30 minutes, treated with N,N-dimethylformamide (0.73 mL) added dropwise over 2 minutes to give a colourless solution, stirred at −78° C. for a further 30 minutes, then removed from the cooling bath and allowed to warm to room temperature over 45 minutes. The solution was quenched by the addition of 10% aqueous ammonium chloride (100 mL), and the resulting mixture was extracted twice with diethyl ether. The combined organic phases were washed with brine, dried over anhydrous magnesium sulphate and concentrated in vacuo to afford the titled compound as a pale yellow oil. Yield 1.74 g.

출처