Diethyl Ether → HCID 86680838, compound

HRID 2401698Notes

Reaction equation

HRID 2401698 reaction equation
[CH2:1]([O:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)[CH3:2].[CH2:16]([O:18]CC)C.C([Li])CCC.CN(C=O)C>O>[CH2:1]([O:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:9]=[CH:10][C:11]=1[CH:16]=[O:18])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 70652002HCID 70652002, compoundHCID 178418339Butyllithium

Product 1

HCID 86680838HCID 86680838, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4.0 g of 1-ethoxymethoxy-3-trifluoromethylbenzene and 160 ml of diethyl ether was added dropwise 16 ml of n-butyllithium (1.6 N, n-hexane solution) under a nitrogen atmosphere at −70° C. This mixture was stirred at room temperature for 3 hours. Subsequently, 5.5 ml of DMF was added to this mixture at −70° C., and the temperature was returned to room temperature. The reaction mixture was added to water. This mixture was extracted twice with ethyl acetate. The organic layers were combined and washed with water and saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.90 g of 2-ethoxymethoxy-4-(trifluoromethyl)benzaldehyde.

Workup

  1. customwas returned to room temperature
  2. extractionThis mixture was extracted twice with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de2cdaacf2db4676b7a061dff0c1895a
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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