2-(Cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehyde → 1-[2-(Cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-phenyl]-ethanol

HRID 604101Notes

Reaction equation

HRID 604101 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:18][CH2:19][CH3:20])[C:6]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:7]=2[CH:8]=[O:9])[CH2:3][CH2:2]1.[CH3:21][Mg]Br>C(OCC)C>[CH:1]1([CH2:4][N:5]([CH2:18][CH2:19][CH3:20])[C:6]2[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][C:7]=2[CH:8]([OH:9])[CH3:21])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 866267692-(Cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 670872311-[2-(Cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-phenyl]-ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2-(Cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehyde (6.0 g) is dissolved in diethylether (50 ml) and thereto is added a 2M methyl magnesium bromide in diethylether (7.35 ml) under nitrogen flow at −70° C. The mixture is stirred at the same temperature for 30 minutes, and the reaction solution is quenched with a saturated aqueous ammonium chloride solution and the mixture is extracted with diethylether. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:2) to give 1-[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-phenyl]-ethanol (5.43 g). MS (m/z): 302 [M+H]+

Workup

  1. customthe reaction solution is quenched with a saturated aqueous ammonium chloride solution
  2. extractionthe mixture is extracted with diethylether
  3. washThe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:2)

Sources & evidence

ORD record
ord-0c8ff4e3a4e34345b027b54df66d18bd
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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