Réaction #324444

ord-bb0c2c23aa4c4330afb0e74a34605523

Équation de réaction

[Cl-].[NH4+]
NH4Cl
O=Cc1ccc(C(F)(F)F)o1
5-trifluoromethyl-furan-2-carbaldehyde
[Br-].[CH3][Mg+]
MeMgBr
CC(O)c1ccc(C(F)(F)F)o1
title compound
Rendement 97.8%
CC(O)c1ccc(C(F)(F)F)o1
1-(5-Trifluoromethyl-furan-2-yl)-ethanol
Rendement 97.8%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionthe mixture extracted with EtOAc (2×)
  2. 2
    LavageThe combined organics were washed with brine
  3. 3
    Autredried

Mode opératoire

To 5-trifluoromethyl-furan-2-carbaldehyde (0.76 g, 4.6 mmol) in THF (20 mL) at 0° C. was added MeMgBr (3M in Et2O, 3 mL, 6 mmol) dropwise over 1 h. After an additional 1 h, ½ saturated NH4Cl (aq.) was added and the mixture extracted with EtOAc (2×). The combined organics were washed with brine and dried to give 0.81 g (97%) of the title compound. 1H NMR (CDCl3): 6.74-6.73 (m, 1H), 6.32-6.31 (m, 1H), 4.91 (q, J=6.5 Hz, 1H), 1.57 (d, J=6.6 Hz, 3H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08642583B2uspto-grants-2014_02