Ammonium Chloride → 1-[3-(Cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]ethanol

HRID 1097410Notes

Reaction equation

HRID 1097410 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH:9]=[O:10])[CH2:3][CH2:2]1.[CH3:18][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:9]([OH:10])[CH3:18])[CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:16])[F:17])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 189736983-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 592936281-[3-(Cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]ethanolYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF, dissolved was 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde (24 g, 99 mmol), and 3M CH3MgBr (49 ml, 148 mmol) was added thereto at −78° C. The reaction mixture was neutralized with NH4Cl, and extracted with EA. The extract was washed twice with brine, dried over MgSO4, filtered and evaporated under reduced pressure to remove solvent. The mixture was purified via column chromatography (n-hexane/EA=1/1) to obtain 1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]ethanol (24 g, 94%).

Workup

  1. additionwas added
  2. customat −78° C
  3. extractionextracted with EA
  4. washThe extract was washed twice with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto remove solvent
  9. customThe mixture was purified via column chromatography (n-hexane/EA=1/1)

Sources & evidence

ORD record
ord-b4185e144bde4cb2a5c0b393ea4730b5
Source dataset
uspto-grants-2012_03
Patent number
US08143262B2

Reaction notes

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