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

HRID 1187142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1187142
[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

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 866473226-bromo-N-methyl-N,5-bis(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide

Produkt 1

HCID 772312476-bromo-5-methoxy-3,4-dihydro-1H-isochromene-1-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

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.

Aufarbeitung

  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 crude 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carbaldehyde was used for next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-cff9f47ef1394269914c5e7677025c15
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673920B2

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