Methyl iodide → Ethyl 4-methoxycyclohexane-1-carboxylate

Into a 100-mL round-bottom flask, was placed a solution of ethyl 4-hydroxycyclohexane-1-carboxylate (1 g, 5.81 mmol) in tetrahydrofuran (20 mL). Sodium hydride (349 mg, 8.72 mmol, 60%) was added to the reaction at 0° C. in portions, then stirred for 20 min. This was followed by the addition of CH3I (865 μL, 11.6 mmol) at 0° C. The reaction mixture was stirred overnight at room temperature, quenched with 6 mL of brine and extracted with 3×40 mL of ether. The combined organic layers were washed with 2×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 800 mg (74%) of the title compound as a colorless oil.

1. customInto a 100-mL round-bottom flask, was placed
2. stirringThe reaction mixture was stirred overnight at room temperature
3. customquenched with 6 mL of brine
4. extractionextracted with 3×40 mL of ether
5. washThe combined organic layers were washed with 2×20 mL of brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-da7e49b3bdcc48479e9868d63c9797ce

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2