Potassium Carbonate → HCID 66777037, compound

HRID 2091107Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:18])=[C:13]([C:15](=O)[CH3:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:28]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:18][C:26]([C:27]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:28])=[C:15]([CH3:16])[C:13]=2[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution (500 mL) of 1-[5-(benzyloxy)-2-hydroxyphenyl]ethanone (29.5 g) synthesized in the above-mentioned (1) in N,N-dimethylformamide were added potassium carbonate (41.4 g) and 2-bromo-1-cyclohexylethanone (25.0 g) synthesized in Example A51(1) at room temperature, and the mixture was stirred at 60° C. for 15 hr. The reaction mixture was allowed to cool to room temperature, filtered through celite. Water was added to the filtrate, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a solid. The obtained solid was washed with ethanol-isopropyl ether to give the title object compound (18.0 g, 43%) as a pale-yellow solid.

Workup

customsynthesized in Example A51(1) at room temperature
temperatureto cool to room temperature
filtrationfiltered through celite
additionWater was added to the filtrate
extractionthe mixture was extracted with diethyl ether
washThe extract was washed with saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customto give a solid
washThe obtained solid was washed with ethanol-isopropyl ether

Sources & evidence

ORD record: ord-b98eac17a0b5443eb2f1a08848fab7c0
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436043B2

Reaction notes

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