Diisopropylamine → 2-Acetyl-4-(4-pyridyl)cyclohexanone

HRID 980908Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[N:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.[C:26](C1NC=CN=1)(=[O:28])[CH3:27]>O1CCCC1.CCCCCC>[C:26]([CH:21]1[CH2:20][CH:19]([C:16]2[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=2)[CH2:24][CH2:23][C:22]1=[O:25])(=[O:28])[CH3:27]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3.2 ml of diisopropylamine dissolved in 40 ml of tetrahydrofuran, there was added 14.2 ml of 1.6M solution of n-butyl lithium in hexane at -20° C. Then, a solution of 2 g of 4-(4-pyridyl)cyclohexanone dissolved in 40 ml of tetrahydrofuran was added at -40° C. The reaction mixture was cooled to -78° C., and 2.5 g of acetylimidazole dissolved in 40 ml of tetrahydrofuran was added. The reaction mixture was stirred at room temperature, poured into ice water, and then washed with ether. The aqueous layer was saturated with ammonium chloride and extracted with methylene chloride. Thus, there was obtained 1.65 g of 2-acetyl-4-(4-pyridyl)cyclohexanone.

Workup

additionwas added at -40° C
additionwas added
washwashed with ether
extractionextracted with methylene chloride

Sources & evidence

ORD record: ord-0db94c5d2858435699da62e6e0524781
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04639521

Reaction notes

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