Methyl iodide → Methyl 2-methyl-2,3-dihydro-1H-indene-2-carboxylate

Temperature

-78 °C

Indane-2-carboxylic acid methyl ester (550 mg, 3.125 mmol) was dissolved in THF (20 mL). At −78° C. LiHMDS (1M solution in THF, 3.75 mL) was added into the reaction mixture. The solution was stirred for 15 min at −78° C., warmed to 0° C. for 15 min and then −78° C. for an additional 15 min. Methyl iodide (250 μL, 4.01 mmol) was then added into the reaction mixture followed by stirring at −78° C. for 15 min, room temperature for 30 min and then quenched with saturated ammonium chloride. The solution was then diluted with diethyl ether and washed with saturated sodium bicarbonate, brine, dried (MgSO4), filtered and concentrated. The crude mixture was then purified by silica gel flash column chromatography to afford 2-methyl-indan-2-carboxylic acid methyl ester (52 mg, 9%) as a white solid. 1H NMR (400 MHz, CDCl3) 7.16 (m, 4H), 3.72 (t, 3H), 3.48 (d, 2H), 2.81 (d, 2H), 1.36 (s, 3H).

1. customAt −78° C
2. temperaturewarmed to 0° C. for 15 min
3. wait−78° C. for an additional 15 min
4. stirringby stirring at −78° C. for 15 min, room temperature for 30 min
5. customquenched with saturated ammonium chloride
6. additionThe solution was then diluted with diethyl ether
7. washwashed with saturated sodium bicarbonate, brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude mixture was then purified by silica gel flash column chromatography

ORD record

ord-7413a577d6ad4e57a4526e707b71299a

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07494999B2