Sodium hydride → 2-[2-(3,4-Dimethoxyphenyl)ethoxy]-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one

HRID 234162Notes

Reaction equation

[OH:1][C:2]1[C:3](=[O:14])[C:4]([CH2:12][OH:13])=[CH:5][CH:6]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:8]=1.[H-].[Na+].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:22][CH2:23]I>CN(C)C=O.ClCCl>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:22][CH2:23][O:1][C:2]2[C:3](=[O:14])[C:4]([CH2:12][OH:13])=[CH:5][CH:6]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:8]=2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-hydroxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one (844 mg, 4.35 mmol) in dimethylformamide (5 ml) was stirred while 60% oily sodium hydride (191 mg, 4.78 mg) in small portions were added thereto. Subsequently, 3,4-dimethoxyphenethyl iodide (2.54 mg, 8.70 mmol) was added, then the solution was heated at 80° C. for 7 hours. The solution was diluted with dichloromethane, washed with water and dried over sodium sulfate. After solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography [eluent:hexane/ethyl acetate (3:2)] to give 169 mg of 2-[2-(3,4-dimethoxyphenyl)ethoxy]-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one as a yellowish brown oil (yield: 11%).

Workup

additionwere added
washwashed with water
dry with materialdried over sodium sulfate
distillationAfter solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography [eluent:hexane/ethyl acetate (3:2)]

Sources & evidence

ORD record: ord-48c6468bbc174b2ab2635fd3860f23b5
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05594144

Reaction notes

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