Methyl iodide → Ethyl 1-methylcyclopentanecarboxylate

Temperature

-78 °C

A solution of nBuLi in hexanes (242 mL, 387 mmol) was added to a −78° C. solution of thisopropylamine (39.1 g, 387 mmol) in anhydrous THF (300 mL) and the resultant mixture was stirred for 30 min at −78° C. A solution of ethyl cyclopentanecarboxylate (50 g, 352 mmol) in anhydrous THF (150 mL) was added dropwise into the mixture and the reaction mixture was stirred at −78° C. for 1 h. Iodomethane (79.2 g, 558 mmol) was added dropwise and the resulting mixture was warmed to RT and stirred overnight The mixture was poured into water and extracted with ethyl ether. The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give ethyl 1-methylcyclopentanecarboxylate (47 g, 85%). 1H NMR (300 MHz, DMSO-d6): δ 4.03 (q, J=7.2 Hz, 2 H), 1.37-2.03 (m, 8 H), 1.15-1.12 (m, 6H).

1. temperaturethe resulting mixture was warmed to RT
2. stirringstirred overnight The mixture
3. extractionextracted with ethyl ether
4. washThe combined extracts were washed with brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo

ORD record

ord-5facdc37e6654d1596481ea6a5e444ca

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188113B2