Borane → HCID 178455782, compound

Borane in THF (1 M, 64.1 mL, 64.1 mmol) was added dropwise to trans-4-ethylcyclohexanecarboxylic acid (10.0 g, 64.1 mmol) in dry THF (100 mL) at −60° C. under a nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred for 12 h. The reaction was quenched with saturated ammonium chloride solution at 0° C., diluted with water (200 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was washed with water (2×200 mL) and brine (100 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to obtain (trans-4-ethylcyclohexyl)methanol. 1H NMR (300 MHz, CDCl3): δ 3.44 (d, J=6.0 Hz, 2H); 1.85-1.70 (dd, J=1.19, 10.5 Hz, 4H); 1.50-1.35 (m, 1H); 1.30-1.10 (m, 4H); 0.95-0.85 (m, 6H).

1. customThe reaction was quenched with saturated ammonium chloride solution at 0° C.
2. additiondiluted with water (200 mL)
3. extractionextracted with ethyl acetate (3×100 mL)
4. washThe organic layer was washed with water (2×200 mL) and brine (100 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-90aba81a927f46d7bf04d469319c4eb9

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846657B2