Ethyl 2-methylbenzo[d]oxazole-7-carboxylate → (2-Methyl-1,3-benzoxazol-7-yl)methanol

HRID 2069678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069678
[CH3:1][C:2]1[O:3][C:4]2[C:10]([C:11](OCC)=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][C:2]1[O:3][C:4]2[C:10]([CH2:11][OH:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Komponenten

4

Edukt 2

HCID 12157468Ethyl 2-methylbenzo[d]oxazole-7-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 58566559(2-Methyl-1,3-benzoxazol-7-yl)methanolAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ethyl 2-methylbenzo[d]oxazole-7-carboxylate (743) (1.27 g, 6.19 mmol) in tetrahydrofuran (61 mL) at 0° C. was added lithium aluminum hydride (7.43 mL, 7.43 mmol, 1M in tetrahydrofuran). The reaction was stirred at 0° C. for 1 hour and quenched with 0.6 mL of water, 0.6 mL of 15% NaOH and 1.8 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 was removed in vacuo to provide (2-methylbenzo[d]oxazol-7-yl)methanol (744) (0.687 g, 68%).

Aufarbeitung

  1. customquenched with 0.6 mL of water, 0.6 mL of 15% NaOH and 1.8 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 was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-713d1c07be6b4bbba9cb40ba5f961840
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299117B2

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