Methyl iodide → Methyl 1-methyl-2-cyclohexene-1-carboxylate

Temperature

78 °C

To a cold (0° C.) solution of freshly distilled N-isopropylpropan-2-amine (4.20 mL, 29.96 mmol) in THF (150 mL) under argon was added dropwise nBuLi (12.65 mL of 2.2 M solution, 27.82 mmol). After 15 min the solution was cooled to 78° C. and dry HMPA (4.84 mL, 27.82 mmol) was added. The mixture was stirred for 30 min at 78° C. and methyl cyclohexene-1-carboxylate (3.00 g, 21.40 mmol) was then added. After stirring an additional 10 min, methyl iodide (2.00 mL, 32.10 mmol) was added. The solution was then allowed to warm to 5° C. over 2 h. An aqueous saturated solution of NH4Cl was poured into the orange mixture. After dilution with hexanes and washing with brine, the organic layer was dried over Na2SO4 and carefully evaporated to 3.3 g of generate methyl 1-methylcyclohex-2-ene-1-carboxylate, 66a, which was used without further purification.

1. stirringAfter stirring an additional 10 min
2. temperatureto warm to 5° C. over 2 h
3. washAfter dilution with hexanes and washing with brine
4. dry with materialthe organic layer was dried over Na2SO4
5. customcarefully evaporated to 3.3 g of generate methyl 1-methylcyclohex-2-ene-1-carboxylate, 66a, which
6. customwas used without further purification

ORD record

ord-b0761336a40643e79e06c4e7454b7c29

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09345708B2