Diisobutylaluminum hydride → HCID 86647314, compound

HRID 1474290Notes

Reaction equation

HRID 1474290 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([C:14](N(C)OC)=[O:15])[O:7][CH2:6][CH2:5]2.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([CH:14]=[O:15])[O:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86647313HCID 86647313, compound

Product 1

HCID 86647314HCID 86647314, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 6-bromo-N-methyl-N,7-bis(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide (800 mg, 2.4 mmol) in 20 mL of anhydrous THF was cooled to −78° C. and then DIBAL-H (4.8 mL, 4.8 mmol, 1M) was added. The mixture was stirred at −78° C. for 1 h. 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 resulting 6-bromo-7-(methyloxy)-3,4-dihydro-1H-isochromene-1-carbaldehyde was used without further purification.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting 6-bromo-7-(methyloxy)-3,4-dihydro-1H-isochromene-1-carbaldehyde was used without further purification

Sources & evidence

ORD record
ord-dbf12d0b72654ce08a0c06ba936d0125
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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