Ammonium Chloride → HCID 74369002, compound

HRID 711332Notes

Reaction equation

HRID 711332 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=[O:7].[CH2:17]([Mg]Br)[CH:18]=[CH2:19].[NH4+].[Cl-]>C1COCC1>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:6]([OH:7])[CH2:19][CH:18]=[CH2:17])[CH:8]=[C:9]([C:11]([F:14])([F:12])[F:13])[CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 74369002HCID 74369002, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-bis(trifluoromethyl)benzaldehyde (10 g, 41 mmol) in THF (100 mL) was drop wise added allylmagnesium bromide (50 mL, 1 M in THF, 50 mmol) at −40° C. The reaction mixture was stirred at room temperature for 5 h and then poured into saturated aqueous NH4Cl solution and extracted with EtOAc (2×100 mL). The organic layers were dried over anhydrous Na2SO4 and then concentrated in high vacuum. The residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1) to give the title compound (800 mg, yield: 7%).

Workup

  1. customat −40° C
  2. extractionextracted with EtOAc (2×100 mL)
  3. dry with materialThe organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated in high vacuum
  5. customThe residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1)

Sources & evidence

ORD record
ord-aaa93e891191495299a2f52dc32c3db3
Source dataset
uspto-grants-2015_11
Patent number
US09181259B2

Reaction notes

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