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

HRID 1187021Notes

Reaction equation

HRID 1187021 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12](N(C)OC)=[O:13].CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[CH:12]=[O:13]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 866473105-bromo-N-methyl-N-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide

Product 1

HCID 772312485-bromo-3,4-dihydro-1H-isochromene-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of 5-bromo-N-methyl-N-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide (3.0 g, 10 mmol) in 60 mL of anhydrous THF was cooled to −30° C. and then DIBAL-H (20 mmol) was added. The mixture was stirred at −30° C. for 1 hours. The reaction was quenched with water, extract with DCM. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The crude 5-bromo-3,4-dihydro-1H-isochromene-1-carbaldehyde was used for next step without purification.

Workup

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

Sources & evidence

ORD record
ord-39d67bb333dc41f1a76f34deebd1d7db
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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