1-Indanone → 2-Methylindanone

Temperatur

-78 °C

To a solution of diisopropylamine (2.06 mL, 14.6 mmol) in THF (14 mL) at 0° C. was a solution of n-butyl lithium (5.55 mL of a 2.5 M in solution in hexanes; 14.6 mmol), dropwise over 15 min. Meanwhile, a solution of 2-methyl-1-indanone (2.03 g, 13.9 mmol) in THF (10 mL) was prepared and cooled to −78° C. under N2. After 30 minutes the above solution of LDA was cooled to −78° C. and added to the above solution of indanone, dropwise over 15 min via double-ended needle. The mixture was stirred 30 min and methyl cyanoformate (1.32 mL, 16.7 mmol) was added. The mixture was stirred 40 minutes, gradually warming ca. to −20° C., quenched with satd NH4Cl and extracted with Et2O (2×25 mL). Combined organics were washed (brine), dried over Na2SO4 and concentrated in vacuo, affording the title compound which was used without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 1.52 (s, 3H), 3.00 (d, J=17.3 Hz, 1 H), 3.67-3.73 (m, 4H), 7.41 (t, J=7.57 Hz, 1H), 7.47 (m, 1H), 7.63 (m, 1 H), 7.79 (d, J=7.57 Hz, 1 H).

1. customat 0° C.
2. stirringThe mixture was stirred 40 minutes
3. temperaturegradually warming ca. to −20° C.
4. customquenched with satd NH4Cl
5. extractionextracted with Et2O (2×25 mL)
6. washCombined organics were washed (brine)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated in vacuo

ORD-Eintrag

ord-a78e7e593c0f430a81e9fb40ea85cb19

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08822518B2