Cesium fluoride → 1-Cyclopropylmethyl-4-cyclopropylmethylsulfanylcyclohex-3-enecarbonitrile

To a solution of 1-cyclopropylmethyl-4-triisopropylsilanylsulfanylcyclohex-3-enecarbonitrile (20.5 g, 58.5 mmol) and (bromomethyl)cyclopropane (15.8 g, 117 mmol) in anhydrous N,N-dimethylformamide (65 ml) was added cesium fluoride (17.8 g, 117 mmol) and the mixture left to stir at ambient temperature for 15 hours. The mixture was diluted with water (500 ml) and extracted with diethyl ether (3×200 ml). The combined organic layer was washed with water (2×300 ml) and brine (200 ml), dried over anhydrous magnesium sulphate, filtered and evaporated to give an orange oil. The oil was purified by dry flash column chromatography on silica eluting with isohexane on a gradient of dichloromethane (10-40%). Collecting appropriate fractions gave a colourless oil (10.7 g, 74%). 1H NMR δ (ppm)(CDCl3): 5.53 (1H, t, J=1.6 Hz), 2.69-2.51 (4H, m), 2.30-2.11 (3H, m), 1.71-1.67 (1H, m), 1.60-1.45 (2H, m), 1.05-0.99 (1H, m), 0.92-0.88 (1H, m), 0.60-0.56 (4H, m), 0.26-0.18 (4H, m).

1. waitthe mixture left
2. extractionextracted with diethyl ether (3×200 ml)
3. washThe combined organic layer was washed with water (2×300 ml) and brine (200 ml)
4. dry with materialdried over anhydrous magnesium sulphate
5. filtrationfiltered
6. customevaporated
7. customto give an orange oil
8. customThe oil was purified
9. dry with materialby dry flash column chromatography on silica eluting with isohexane on a gradient of dichloromethane (10-40%)
10. customCollecting appropriate fractions

ORD record

ord-d4aa50c5ff1c40b9ba3ca69e3b55bf48

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07626056B2