Diisobutylaluminum hydride → 6-bromo-5-methoxy-3,4-dihydro-1H-isochromene-1-carbaldehyde

HRID 1474399Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12](N(C)OC)=[O:13])[O:7][CH2:6][CH2:5]2.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH:12]=[O:13])[O:7][CH2:6][CH2:5]2

Participants

Conditions

Temperature: -30 °C

Procedure

To a solution of 6-bromo-N-methyl-N,5-bis(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide (300 mg, 0.9 mmol) in 20 mL of anhydrous THF was cooled to −30° C. and then DIBAL-H (1.3 mL, 1.3 mmol, 1M) was added. The mixture was stirred at −30° C. for 2 hours. The reaction was quenched with water and extracted with DCM. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The crude 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carbaldehyde was used for next step without purification.

Workup

customThe reaction was quenched with water
extractionextracted with DCM
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe crude 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carbaldehyde was used for next step without purification

Sources & evidence

ORD record: ord-b450afb7d6e149eeabee3f7502b7e991
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018211B2

Reaction notes

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