Aluminium lithium hydride → (5-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol

HRID 1909559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909559
[Br:1][C:2]1[CH:3]=[C:4]([C:13](OC)=[O:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][OH:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 58566735Methyl 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate

Produkt 1

HCID 58566787(5-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of methyl 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (668) (466 mg, 1.63 mmol) in tetrahydrofuran (16 mL) at 0° C. was added LAH (1 mL, 1.96 mmol). The reaction was stirred at 0° C. for 1 hour and quenched with 0.2 mL of water, 0.2 mL of 15% NaOH and 0.6 mL of water. The reaction was warmed to room temperature and diluted with diethyl ether. Magnesium sulfate was added and the solution was filtered, washed with diethyl ether, and the solvent removed in vacuo to provide (5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol (669).

Aufarbeitung

  1. customquenched with 0.2 mL of water, 0.2 mL of 15% NaOH and 0.6 mL of water
  2. temperatureThe reaction was warmed to room temperature
  3. additiondiluted with diethyl ether
  4. additionMagnesium sulfate was added
  5. filtrationthe solution was filtered
  6. washwashed with diethyl ether
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5ff7e93728ef4ac1862c2e061bd6e370
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598374B2

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