Ammonium → HCID 22933610, compound

Temperature

0 °C

Under a nitrogen atmosphere, a 2M-lithium diisopropylamide solution (7.32 ml, 0.0146 mmol) was added dropwise to a solution of methyl cis-3-methoxycyclohexane-carboxylate (1.80 g, 0.0105 mol) in tetrahydrofuran (36 ml) at −78° C. over a period of 15 minutes. After 3 hours, a solution of methyl iodide (4.45 g, 0.0314 mmol) in tetrahydrofuran (9 ml) was added dropwise thereto over a period of 20 minutes, and the resulting mixture was slowly warmed up to 0° C. After 3 hours, a saturated aqueous ammonium solution was added thereto and the resulting mixture was poured into water and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain methyl 3-methoxy-1-methylcyclohexanecarboxylate (1.8985 g, 98%, a 4:1 mixture of isomers).

1. waitover a period of 20 minutes
2. waitAfter 3 hours
3. extractionextracted with ethyl acetate
4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
5. customThe organic layer dried
6. concentrationwas concentrated under reduced pressure
7. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

ORD record

ord-367f380fef9440ea94d32aad91288a4c

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2