Trimethylsilyl cyanide → HCID 20471684, compound

2-Methyl-1-cyclohexene-1-carbaldehyde (3.7 g., 29.8 mmole), trimethylsilyl cyanide (4.7 ml., 1.25 equivalents) and 50 mg. of zinc iodide were stirred in 50 ml. of ether for 1.5 hours at room temperature. The reaction mixture was filtered over diatomaceous earth and the filtrate concentrated in vacuo. The residual trimethylsilyl ether was taken up in 50 ml. acetone and acidified with 5 ml. 6N HCl. The mixture was stirred for 3 hours at room temperature, diluted with 500 ml. of ether, and the aqueous layer separated and discarded. The organic layer was washed 1×50 ml. saturated NaHCO3, dried over Na2SO4 and concentrated to an oil (3.2 g.). The oil was chromatographed on 100 ml. silica gel initially with 9:1, then 4:1, then 2:1 hexane:ethyl acetate and finally ethyl acetate as eluant. Product fractions were combined and evaporated to yield title product as an oil, 800 mg.

1. filtrationThe reaction mixture was filtered over diatomaceous earth
2. concentrationthe filtrate concentrated in vacuo
3. additiondiluted with 500 ml
4. customof ether, and the aqueous layer separated
5. washThe organic layer was washed 1×50 ml
6. dry with materialsaturated NaHCO3, dried over Na2SO4
7. concentrationconcentrated to an oil (3.2 g.)
8. customThe oil was chromatographed on 100 ml
9. customevaporated

ORD record

ord-838ad4aff1354c91bcc837b3a5691490

Source dataset

uspto-grants-1984_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04430337