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Chlorotrimethylsilane → Methyl-4-oxo-4-[4'-(trifluoromethoxy)-1,1'-biphenyl-4-yl]butanoate

HRID 28334
Notes
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Reaction equation

HRID 28334 reaction equation
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:25]OC(OC)(C)C.C[Si](Cl)(C)C>CO>[CH3:25][O:6][C:5](=[O:7])[CH2:4][CH2:3][C:2](=[O:1])[C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:22])([F:23])[F:24])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 64952,2-DimethoxypropaneHCID 120568834-Oxo-4-[4'-(trifluoromethoxy)-1,1'-biphenyl-4-yl]butyric acid

Product 1

HCID 11256659Methyl-4-oxo-4-[4'-(trifluoromethoxy)-1,1'-biphenyl-4-yl]butanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Crude 4-oxo-4-[4′-(trifluoromethoxy)-1,1′-biphenyl-4-yl]butyric acid (25 g, content: 65%, GC, silylated, 100% method) is dissolved in a mixture of methanol (50 ml) and 2,2-dimethoxypropane (11.5 g, 110 mmol), treated with trimethylsilyl chloride (0.75 g, 7 mmol) and stirred at 50° C. for 16 h. The reaction mixture is then concentrated and the residue is recrystallized from toluene.

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. customthe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-94a7ac36b8a0497681810865690b64ae
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07419936B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes