Diethyl Ether → HCID 57812285, compound

HRID 912025Notes

Reaction equation

HRID 912025 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:3]=1[CH:4]=[O:5].[CH3:14][Mg]Br.CCOCC.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[C:3]=1[CH:4]([OH:5])[CH3:14]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 177506792-Chloro-6-(trifluoromethyl)benzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 57812285HCID 57812285, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-6-(trifluoromethyl)benzaldehyde (266.9 mg, 1.280 mmol, 1 eq) in anhydrous THF (5 mL) at 0° C. under nitrogen, a 3.0 M solution of methylmagnesium bromide in Et2O (0.50 mL, 1.5 mmol, 1.2 eq) was added and the reaction was allowed to stir and warm to ambient temperature overnight. The reaction mixture was again cooled to 0° C. and saturated NH4Cl was added. Diethyl ether was also added and the layers were separated. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The colorless oil crude was purified by chromatography on silica gel [0.5″×10″ glass column, eluting with 1:1 CH2Cl2:Heptane]. Fractions containing product were combined and concentrated in vacuo, affording the title material as a clear and colorless oil. 1H NMR (400 MHz, CDCl3) δ=1.73 (d, J=6.8 Hz, 3H), 3.04 (br s, 1H), 5.43 (q, J=6.8 Hz, 1H), 7.33 (ddq, J=8.0, 8.0, 0.8 Hz, 1H), 7.59 (d, J=7.8 Hz, 1H), 7.63 (d, J=7.8 Hz, 1H). MS (ES+): m/z 248.01/250.03 (100/37) [MNa+]. HPLC: tR=3.26 min (ZQ3, polar—5 min).

Workup

  1. temperatureThe reaction mixture was again cooled to 0° C.
  2. customthe layers were separated
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe colorless oil crude was purified by chromatography on silica gel [0.5″×10″ glass column
  8. washeluting with 1:1 CH2Cl2
  9. additionFractions containing product
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-247d52c087a946dbb9fa5882559fe3ef
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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