Ammonium Chloride → HCID 67347495, compound

HRID 237262Notes

Reaction equation

HRID 237262 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[O:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=1.[CH3:12][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[F:11][C:2]([F:10])([F:1])[C:3]1[O:7][C:6]([CH:8]([OH:9])[CH3:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 75376655-(trifluoromethyl)furan-2-carbaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 67347495HCID 67347495, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. extractionthe mixture extracted with EtOAc (2×)
  2. washThe combined organics were washed with brine
  3. customdried

Sources & evidence

ORD record
ord-bb0c2c23aa4c4330afb0e74a34605523
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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