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

HRID 2173265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173265
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

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, extracted 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.

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 5-bromo-3,4-dihydro-1H-isochromene-1-carbaldehyde was used for next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-d9f4cfa9e4474008a9540fd49d0de689
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

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