Dimethyl Sulfate → 4-Pentylcyclohexanol methyl ether

Temperature

0 °C

Under argon, to a solution of 4-pentylcyclohexanol (2.0 g, 11.75 mmol) in anhydrous THF (60 mL), NaH was added (60%, 0.94 g, 23.5 mmol) at 0° C. and stirred for 30 minutes, followed by the addition of dimethyl sulfate (1.68 mL, 17.62 mmol). The mixture was refluxed for 12 hrs and cooled to 0° C. The reaction was quenched with saturated ammonium chloride solution (20 mL). THF was removed under vacuum and the residue was extracted with CH2Cl2 (3×25 mL). The collected organic portion was dried with Na2SO4 and concentrated. The crude product was purified by flash chromatography (hexanes/ethyl acetate: 15/1) to provide probe 1 (2.0 g, quant.) as a colorless liquid. 1H NMR (400 MHz, CDCl3): δ=0.79-0.85 (m, 10 H), 1.28-1.38 (m, 7 H), 1.46 (br, 2 H), 2.02 (br, 2 H), 3.32 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ=8.1, 20.9 (2 carbons), 24.1 (2 carbons), 30.2 (2 carbons), 32.6, 34.8, 45.2, 55.5, 74.8; MS (ESI) calcd for C12H25O [M+H]+/z: 185.19. found: 185.31.

1. temperatureThe mixture was refluxed for 12 hrs
2. customThe reaction was quenched with saturated ammonium chloride solution (20 mL)
3. customTHF was removed under vacuum
4. extractionthe residue was extracted with CH2Cl2 (3×25 mL)
5. dry with materialThe collected organic portion was dried with Na2SO4
6. concentrationconcentrated
7. customThe crude product was purified by flash chromatography (hexanes/ethyl acetate: 15/1)
8. customto provide probe 1 (2.0 g, quant.) as a colorless liquid

ORD record

ord-28842b710f4c409d9ba7fd00e14e0a53

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273342B2