Hydrochloric Acid → 2,2,2-Trifluoro-1-(3'-methylbiphenyl-2-yl)ethanol

HRID 469888Notes

Reaction equation

HRID 469888 reaction equation
C[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[CH:14]=[O:15].[F:16][C:17]([Si](C)(C)C)([F:19])[F:18].Cl.[CH2:25]1COCC1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:16][C:17]([F:19])([F:18])[CH:14]([C:3]1[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=1[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([CH3:25])[CH:13]=1)[OH:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 1869592-Methyl-6-phenylbenzaldehydeHCID 552549(Trifluoromethyl)trimethylsilane

Product 1

HCID 666492512,2,2-Trifluoro-1-(3'-methylbiphenyl-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideCatalyst

Procedure

Alternatively, tetrabutylammoniumfluoride (TBAF 1.0 N in THF 13 uL, 3.3 mg, 0.013 mmol) was added to a mixture of 3-methyl-biphenyl-2-carboxaldehyde (0.25 g, 1.27 mmol) and trifluoromethytrimethyl silane (0.25 g, 1.53 mmol), in THF (1.5 ml) at 0° C. The reaction was warmed to room temperature and stirred for 4 hours. HCl (3.0 N, 2.0 ml) was added, and the mixture was stirred for 3 hours. The mixture was concentrated, dissolved in methylene chloride, filtered through silica gel, and concentrated to give 0.15 g of 2,2,2-trifluoro-1-(3′-methylbiphenyl-2-yl)ethanol.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in methylene chloride
  4. filtrationfiltered through silica gel
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b90e96e8454482b89ac42b894232d6f
Source dataset
uspto-grants-2014_01
Patent number
US08629156B2

Reaction notes

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