Methyl iodide → HCID 59609123, compound

Temperature

-78 °C

Trimethyl[(2R,3S)-3-(naphthalene-2-yl) oxirane-2-yl]silane (9.8 μg, 0.40 mmol) was dissolved in THF anhydride (1.6 mL) in a nitrogen atmosphere and the resultant solution was cooled down to −78° C. Thereinto, n-butyl lithium (2.69 molL−1 in 180.3 μL, 0.48 mmol of hexane solution) was dropped and the resultant reaction mixture was stirred at −78° C. for 90 minutes. Thereto, methyl iodide (99.8 μL, 1.60 mmol) was added and the resultant reaction mixture was stirred at −78° C. for 15 minutes. Thereafter, the reaction mixture was returned to the room temperature and was further stirred for 1 hour. The reaction was quenched with water and the resultant mixture was extracted with ethyl acetate. The organic phase was washed with water and saline and was dried over Na2SO4. The obtained crude product was purified by silica gel column chromatography (n-pentane/diethyl ether=0/0) to produce trimethyl [(2R,3S)-3-methyl-3-(naphthalene-2-yl) oxirane-2-yl]silane in a yield of 71%. Trimethyl[(2R,3S)-3-methyl-3-(naphthalene-2-yl) oxirane-2-yl]silane

1. customthe resultant reaction mixture
2. customthe resultant reaction mixture
3. stirringwas stirred at −78° C. for 15 minutes
4. customwas returned to the room temperature
5. stirringwas further stirred for 1 hour
6. customThe reaction was quenched with water
7. extractionthe resultant mixture was extracted with ethyl acetate
8. washThe organic phase was washed with water and saline
9. dry with materialwas dried over Na2SO4
10. customThe obtained crude product
11. customwas purified by silica gel column chromatography (n-pentane/diethyl ether=0/0)

ORD record

ord-2dae1155693f42b486088be9bf4fde24

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217184B2