Cyclohexanecarboxaldehyde → 1-Cyclohexylprop-2-en-1-ol

Temperature

-20 °C

A solution of cyclohexanecarbaldehyde (4.79 mL, 39.8 mmol) in tetrahydrofuran (30 mL) was added dropwise to a solution of vinylmagnesium bromide (47.8 mL, 1M in tetrahydrofuran, 47.8 mmol) stirring at −20° C. The solution was stirred for 30 minutes at −20° C. at which time saturated ammonium chloride solution (75 mL) was added and the reaction was allowed to warm to 25° C. The solution was diluted with water and extracted three times with ethyl acetate. The ethyl acetate layers were combined and washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane, followed by 5% and 10% ethyl acetate in hexane to give the title compound (2.11 g, 38%). 1H NMR (300 MHz, CDCl3): δ ppm 1.40 m, 11 H) 3.85 (m, 1 H) 5.17 m, 2 H) 5.86 m, 1 H).

1. additionwas added
2. temperatureto warm to 25° C
3. extractionextracted three times with ethyl acetate
4. washwashed with brine
5. dry with materialdried with sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was chromatographed on silica gel eluting with hexane

ORD record

ord-39ae4839f27f463e8b64b2c72968e046

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07378414B2