Ethyl Acetate → HCID 22998966, compound

HRID 1166603Notes

Reaction equation

[CH3:1]CCCCC.C([Li])CCC.[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[O:23][CH2:22][C:21]3[N:24]=[CH:25][CH:26]=[CH:27][C:20]=3[C:19](=O)[C:18]=2[CH:29]=1.[Cl-].[NH4+].C(OCC)(=O)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[O:23][CH2:22][C:21]3[N:24]=[CH:25][CH:26]=[CH:27][C:20]=3[C:19](=[CH2:1])[C:18]=2[CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyltriphenylphosphonium bromide (2.2 g) in THF (20 ml) was added 1.6M n-butyl lithium hexane solution (2.9 ml) at 0° C. for 30 minutes. To the reaction mixture cooled to 0° C. was added 5,11-dihydro-7-methoxypyrido[2,3-c][1]benzoxepin-5-one (1.0 g) dropwise as THF solution (5 ml), and the mixture was warmed to room temperature, and stirred for 3 hours. Aqueous ammonium chloride and ethyl acetate were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (1:4) to give 5,11-dihydro-7-methoxy-5-methylenepyrido[2,3-c][1]benzoxepine (0.14 g).

Workup

temperaturethe mixture was warmed to room temperature
customthe organic layer was separated
washwashed with saturated aqueous sodium chloride
dry with materialdried with magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel chromatography
washeluting with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record: ord-c13fb0c167a84bf7a58cbfc4eb4c89ea
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613905B1

Reaction notes

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