Methyl iodide → 4-Methylthiane-4-carbonitrile

A solution of tetrahydro-thiopyran-4-carbonitrile (3.05 g, 24 mmol) in anhydrous tetrahydrofuran (60 ml) was cooled to −78° C. and treated with lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 26.4 ml, 26.4 mmol) dropwise. After 30 minutes of stirring, iodomethane (1.8 ml, 29 mmol) was added dropwise. The cooling bath was removed, and the reaction mixture was allowed to slowly rise to room temperature and stir overnight. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving an orange oil. The oil was purified by silica gel chromatography using 5-50% EtOAc in hexanes as eluant to provide 1.81 g (53%) of 4-methyl-tetrahydro-thiopyran-4-carbonitrile as a colorless oil.

1. customThe cooling bath was removed
2. customto slowly rise to room temperature
3. stirringstir overnight
4. customThe reaction mixture was quenched with saturated aqueous NH4Cl
5. extractionextracted with EtOAc
6. customThe organic layers were collected
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customgiving an orange oil
11. customThe oil was purified by silica gel chromatography

ORD record

ord-90cd095f84b949b9bafdd17d6a3c678a

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008298B2