Diisobutylaluminum hydride → 5-Methyl-2-(trifluoromethyl)-3-furanmethanol

HRID 237252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237252
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[O:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=O)C.CC(C[AlH]CC(C)C)C>CCOCC>[CH3:11][C:9]1[O:8][C:7]([C:12]([F:15])([F:13])[F:14])=[C:6]([CH2:4][OH:3])[CH:10]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 2737208Ethyl 5-methyl-2-(trifluoromethyl)furan-3-carboxylate

Produkt 1

HCID 27798975-Methyl-2-(trifluoromethyl)-3-furanmethanolAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 5-methyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester (0.83 g, 3.7 mmol) in Et2O at 0° C., was added DIBAL-H (1.0 M in THF, 1.5 mL). After 10 min, the ice bath was removed and additional DIBAL-H was added (1.0 M in THF, 14.5 mL). After 2 h, the reaction was quenched with a saturated solution of sodium potassium tartrate (aq.) and allowed to stir overnight. After 18 h, EtOAc was added and the organic layer separated and dried provide the title compound (0.39 g, 58%). 1H NMR (CDCl3): 6.19 (s, 1H), 4.62 (s, 2H), 2.36-2.28 (m, 3H).

Aufarbeitung

  1. customthe ice bath was removed
  2. additionadditional DIBAL-H was added (1.0 M in THF, 14.5 mL)
  3. waitAfter 2 h
  4. customthe reaction was quenched with a saturated solution of sodium potassium tartrate (aq.)
  5. waitAfter 18 h
  6. additionEtOAc was added
  7. customthe organic layer separated
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8901ed5de1704aa69f65c3f13bdd6fe3
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642583B2

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