N-Formylmorpholine → HCID 59516960, compound

HRID 1698715Notes

Reaction equation

Br[C:2]1[CH:12]=[C:11]([O:13][CH3:14])[C:5]2[O:6][CH2:7][CH2:8][CH2:9][O:10][C:4]=2[C:3]=1[F:15].C([Li])CCC.[CH:21](N1CCOCC1)=[O:22].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[F:15][C:3]1[C:4]2[O:10][CH2:9][CH2:8][CH2:7][O:6][C:5]=2[C:11]([O:13][CH3:14])=[CH:12][C:2]=1[CH:21]=[O:22]

Participants

Conditions

Temperature: -72 °C

Procedure

To a solution of 548 mg of 7-bromo-6-fluoro-9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepine in 15 ml of THF there was added dropwise 0.81 ml of n-butyllithium (2.55 M, hexane solution) at −70° C. under a nitrogen atmosphere. After stirring at −72° C. for 30 minutes, 0.3 ml of N-formylmorpholine was added and the temperature was raised from −78° C. to 0° C. over a period of 30 minutes. Saturated aqueous ammonium chloride was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (239 mg) as a solid.

Workup

temperaturethe temperature was raised from −78° C. to 0° C. over a period of 30 minutes
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationThe desiccating agent was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record: ord-2db67e2bf20f4fb38a1acf57a359c24a
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163787B2

Reaction notes

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