Dimethylformamide → 4-((Tert-butyldimethylsilyl)oxy)-4-methylpent-2-ynal

Temperature

-78 °C

To the solution of 10 g (50 mmol) of 3-(tert.butyldimethylsilyl)oxy-3-methyl-butyne in 25 ml. of anhydrous tetrahydrofuran cooled at -78° C. in an argon atmosphere was added dropwise over a 40 minute period 40 ml (0.64 mmol) 1.6M solution of N-butyl lithium in hexane, which was followed by addition of 31 ml (400 mmol) of N,N-dimethylformamide. The reaction mixture was stirred for an additional one-half hour at -78° C., and then quenched by addition of ice and pouring into 300 ml of brine. It was then extracted with pentane. The pentane extract was washed with saturated ammonium chloride solution, water and brine, dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by distillation at 113°-115° C./25 mmHg. It gave 8.88 g (78%) of the title compound.

1. customquenched by addition of ice
2. additionpouring into 300 ml of brine
3. extractionIt was then extracted with pentane
4. extractionThe pentane extract
5. washwas washed with saturated ammonium chloride solution, water and brine
6. dry with materialdried over anhydrous sodium sulfate
7. customevaporated to dryness
8. distillationThe crude product was purified by distillation at 113°-115° C./25 mmHg

ORD record

ord-a55b3810dc124a58bbac2f8ddb42a16a

Source dataset

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05393900