Diisopropylamine → HCID 21196457, compound

HRID 1067112Notes

Reaction equation

C(NC(C)C)(C)C.[Li]CCCC.[C:13]1(=[O:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH3:20][O:21][C:22]1[C:23]([CH3:30])=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=[O:26]>C1COCC1>[OH:26][CH:25]([C:24]1[CH:27]=[CH:28][CH:29]=[C:22]([O:21][CH3:20])[C:23]=1[CH3:30])[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][C:13]1=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of diisopropylamine (1.44 ml) in THF (8 ml) was added n-BuLi (1.56M solution in hexane, 70 ml) at −60° C. The mixture was warmed to 0° C., stirred for 10 minutes, and recooled to −60° C. To the mixture was added cyclohexanone (0.98 g) in THF (5 ml). After stirring for 1 hour, 3-methoxy-2-methylbenzaldehyde (1.5 g) was added and the mixture was stirred for 1.5 hours at the same temperature. The reaction mixture was quenched with saturated NH4Cl solution, warmed to room temperature, extracted with EtOAc. The organic layer was washed with water and brine, dried over magnesium sulfate, evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 4:1 to 2:1) to give 2-[hydroxy-(3-methoxy-2-methylphenyl)methyl]cyclohexanone (1.86 g) as an oil.

Workup

customrecooled to −60° C
stirringAfter stirring for 1 hour
stirringthe mixture was stirred for 1.5 hours at the same temperature
customThe reaction mixture was quenched with saturated NH4Cl solution
temperaturewarmed to room temperature
extractionextracted with EtOAc
washThe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (hexane-EtOAc 4:1 to 2:1)

Sources & evidence

ORD record: ord-ee14f09175ef4242b56282fb4d29844e
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245790B1

Reaction notes

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