反应详情

3-Dimethylamino-1,2-propanediol (5), (50.1 g, 420.4 mmol) was weighed into a 2 L round bottomed flask with a stir bar. The flask was sealed, flushed with argon, charged with N,N-dimethylformamide (750 mL) and N,N-diisopropylethylamine (111 mL, 630.7 mmol) and cooled to 0° C. t-Butyldimethylchlorosilane (67.0 g, 1.05 equiv.) was weighed into a 500 mL round bottomed flask, sealed and then dissolved in N,N-dimethylformamide (250 mL). The t-butyldimethylchlorosilane solution was transferred to a pressure equalizing dropping funnel and added to the stirring reaction mixture slowly over 20 minutes. The reaction was allowed to come to room temperature while stirring over 3 hours. The reaction was concentrated in vacuo. Saturated bicarbonate (1500 mL) was added to the residue and the mixture transferred to a 4 L separatory funnel. The aqueous phase was extracted with ethyl acetate (3×500 mL). The organic phases were combined, dried over MgSO4, filtered, concentrated and dried under high vacuum to afford 97.81 g (99.7%) of clear, colorless oil that was used without further purification.

1. customThe flask was sealed
2. customflushed with argon
3. customwas weighed into a 500 mL round bottomed flask
4. customsealed
5. additionadded to the stirring reaction mixture slowly over 20 minutes
6. customto come to room temperature
7. concentrationThe reaction was concentrated in vacuo
8. additionSaturated bicarbonate (1500 mL) was added to the residue
9. customthe mixture transferred to a 4 L separatory funnel
10. extractionThe aqueous phase was extracted with ethyl acetate (3×500 mL)
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated
14. customdried under high vacuum
15. customto afford 97.81 g (99.7%) of clear, colorless oil that
16. customwas used without further purification