Dimethylformamide → 1H-Indene-5-carboxaldehyde, 2,3-dihydro-1-(methoxyimino)-

HRID 1268904Notes

Reaction equation

[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.[Li]CCCC.CN([CH:22]=[O:23])C>C1COCC1>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:22]=[O:23])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

Conditions

Temperature: -60 °C

Procedure

To a solution of the product of Step 1 (112 g, 0.46 mol) in THF (1500 ml) at −60° C. under argon, was added n-BuLi (325 ml, 0.52 mol) over 1 hour. After stirring at −60° C. for 1 hour a solution of DMF (39.7 ml) in THF (50 ml) was added dropwise over 1 hour. The reaction was stirred at −60° C. for 1 hour before being allowed to warm to room temperature. After 1 hour the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted into ethyl acetate. The organic phase was then dried (Na2SO4), concentrated in vacuo and the residue purified by silica gel chromatography, to give the title compound (57 g, 65%) as a yellow solid; 1H NMR (CDCl3) 10.0 (1H, s), 7.83–7.73 (3H, m), 4.02 (3H, s), 3.10 (2H, m), 2.92 (2H, m).

Workup

additionwas added dropwise over 1 hour
temperatureto warm to room temperature
customAfter 1 hour the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution
extractionextracted into ethyl acetate
dry with materialThe organic phase was then dried (Na2SO4)
concentrationconcentrated in vacuo
customthe residue purified by silica gel chromatography

Sources & evidence

ORD record: ord-cd987730a5dd4ba183df1092dbed388f
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199137B2

Reaction notes

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