반응 #51962

반응 방정식

4-[(dimethylamino)methyl]benzaldehyde

ammonium chloride

tert-butyl dimethylcarbamate

tetramethylethylenediamine

sec-butyllithium

→

title compound

수율 76.3%

tert-Butyl 2-{4-[(dimethylamino)methyl]phenyl}-2-hydroxyethyl(methyl)carbamate

수율 76.3%

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas introduced
2. 2
   workup.STIRRINGstirred for 1 hour
3. 3
   기타to quench
4. 4
   기타the reaction after the reaction mixture
5. 5
   온도was cooled to −78° C
6. 6
   기타The organic phase was separated
7. 7
   추출the aqueous phase was extracted with dichloromethane
8. 8
   세척washed with brine
9. 9
   건조dried over sodium sulfate
10. 10
    농축concentrated
11. 11
    기타The residue was purified with a silica gel column

실험 절차

To a solution of tert-butyl dimethylcarbamate (350 mg, 2.4 mmol) and tetramethylethylenediamine (511 mg, 4.4 mmol) in THF (anhydrous, 10 mL) was added sec-butyllithium (1.4 M in cyclohexane, 2.2 mL, 3.1 mmol) at −78° C. The mixture was stirred at that temperature for 1 hour before 4-[(dimethylamino)methyl]benzaldehyde (J.Heterocycl.Chem.; 26; 1989; 1325-1330)(280 mg, 1.7 mmol) was introduced. The reaction mixture was stirred for 2 hours, warmed to room temperature and stirred for 1 hour. Saturated ammonium chloride aqueous solution (10 mL) was added to quench the reaction after the reaction mixture was cooled to −78° C. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with brine and dried over sodium sulfate and concentrated. The residue was purified with a silica gel column to give the title compound (0.40 g) as a white solid.

출처