N-Formylmorpholine → HCID 59517315, compound

HRID 1161489Notes

Reaction equation

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

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 1.3 g of 5-bromo-1,2-dimethoxy-3-(2-methoxyethyl)benzene in 20 ml of THF there was added dropwise 2 ml of n-butyllithium (2.66 M, hexane solution) at −70° C. under a nitrogen atmosphere. After stirring at −70° C. for 30 minutes, 0.7 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 (806 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-6bdd2b526aab47a59e04baec1b41cdbd
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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