N-Formylmorpholine → 4-Methoxy-8,9-dihydro-5,7-dioxabenzocycloheptene-2-carbaldehyde

HRID 2079215Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]2[O:11][CH2:10][O:9][CH2:8][CH2:7][C:6]=2[CH:12]=1.C([Li])CCC.[CH:20](N1CCOCC1)=[O:21].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH3:14][O:13][C:4]1[C:5]2[O:11][CH2:10][O:9][CH2:8][CH2:7][C:6]=2[CH:12]=[C:2]([CH:20]=[O:21])[CH:3]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 420 mg of 2-bromo-4-methoxy-8,9-dihydro-5,7-dioxa-benzocycloheptene in 10 ml of THF there was added dropwise 0.7 ml of n-butyllithium (2.66 M, hexane solution) at −70° C. under a nitrogen atmosphere. After stirring at −70° C. for 10 minutes, 0.5 ml of N-formylmorpholine was added and the temperature was raised from −70° 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 (235 mg) as an oil.

Workup

temperaturethe temperature was raised from −70° 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-c1991ec3da184314a963fe73bb09ceac
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928228B2

Reaction notes

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