Diethyl Ether → HCID 22620521, compound

HRID 840971Notes

Reaction equation

CO[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][CH2:5][C:4]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH3:19][Mg]I.C(OCC)C.[Cl-].[NH4+]>O1CCCC1>[CH3:19][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][CH2:5][C:4]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

Conditions

Temperature: -5 °C

Procedure

A solution of ethyl 9-methoxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (4.00 g, 16.2 mmol) in tetrahydrofuran (60 ml) was cooled to −10° C., and methylmagnesium iodide (a 2M diethyl ether solution 16.2 ml, 32.5 mmol) was added dropwise thereto. The reaction mixture was stirred at −5° C. for 2 hours, poured into a cold aqueous ammonium chloride solution and then extracted twice with ethyl acetate. The extract solution was washed with an aqueous sodium hydrogen-carbonate solution and a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98) to obtain 0.81 g of ethyl 9-methyl-6,7-dihydro-5H-benzocycloheptene-8-carboxylate.

Workup

extractionextracted twice with ethyl acetate
washThe extract solution was washed with an aqueous sodium hydrogen-carbonate solution
dry with materiala 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98)

Sources & evidence

ORD record: ord-885e166037484816915c7224fc361bac
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369110B1

Reaction notes

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