Chlorotrimethylsilane → 153587-50-9

Temperature

0 °C

To 3-difluoromethoxy-4-methoxybenzaldehyde (2 g, 9.8 mmol) was added lithium bromide (1.7 g, 19.6 mmol) and acetonitrile (11 mL). Upon dissolution, the reaction mixture was cooled to 0° C. Trimethylsilylchloride (1.86 mL, 14.7 mmol) was slowly added and the reaction mixture was allowed to warm to room temperature and was stirred for 15 min. The reaction mixture was again cooled to (0° C., 1,1,3,3-tetramethyldisiloxane (2.6 mL, 14.7 mmol) was added and the resulting mixture was allowed to warm to room temperature. After stirring for 3 h, the mixture was separated into two layers. The lower layer was removed, diluted with methylene chloride and filtered. The filtrate was concentrated under reduced pressure, dissolved in methylene chloride and refiltered. The solvent was removed in vacuo to provide an oil, which was dissolved in dimethylformamide (10 mL) under an argon atmosphere and treated with sodium cyanide (1.08 g, 22 mmol). The resulting mixture was stirred at room temperature overnight, then poured into cold water (250 mL) and extracted three times with ethyl acetate. The organic extract was washed three times with water, once with brine and was dried (potassium carbonate). The solvent was removed in vacuo to provide a yellow oil (1.54 g, 74%), which was used without purification.

1. dissolutionUpon dissolution
2. temperatureto warm to room temperature
3. additionwas added
4. temperatureto warm to room temperature
5. stirringAfter stirring for 3 h
6. customthe mixture was separated into two layers
7. customThe lower layer was removed
8. additiondiluted with methylene chloride
9. filtrationfiltered
10. concentrationThe filtrate was concentrated under reduced pressure
11. dissolutiondissolved in methylene chloride
12. customThe solvent was removed in vacuo
13. customto provide an oil, which
14. stirringThe resulting mixture was stirred at room temperature overnight
15. extractionextracted three times with ethyl acetate
16. extractionThe organic extract
17. washwas washed three times with water
18. dry with materialonce with brine and was dried (potassium carbonate)
19. customThe solvent was removed in vacuo

ORD record

ord-3c09c9bb14554488a94394a8261cb03a

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05631286