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Trifluoroacetic acid → (4'-{1-Ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-2'-methyl-biphenyl-4-yl)acetic acid methyl ester

HRID 546885
Notes
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Reaction equation

HRID 546885 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:52])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH2:49][CH3:50])([C:27]3[CH:32]=[CH:31][C:30]([C:33]#[C:34][C:35]([O:44]COC)([C:40]([F:43])([F:42])[F:41])[C:36]([F:39])([F:38])[F:37])=[C:29]([CH3:48])[CH:28]=3)[CH2:25][CH3:26])=[CH:20][C:19]=2[CH3:51])=[CH:14][CH:13]=1>ClCCl>[CH3:8][O:9][C:10](=[O:52])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH2:25][CH3:26])([C:27]3[CH:32]=[CH:31][C:30]([C:33]#[C:34][C:35]([OH:44])([C:40]([F:41])([F:43])[F:42])[C:36]([F:39])([F:37])[F:38])=[C:29]([CH3:48])[CH:28]=3)[CH2:49][CH3:50])=[CH:20][C:19]=2[CH3:51])=[CH:14][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57709204(4'-{1-Ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-methoxymethoxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-2'-methyl-biphenyl-4-yl)acetic acid methyl ester

Product 1

HCID 57709077(4'-{1-Ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-2'-methyl-biphenyl-4-yl)acetic acid methyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Trifluoroacetic acid (0.2 mL) was added to a solution of (4′-{1-ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-methoxymethoxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-2′-methyl-biphenyl-4-yl)acetic acid methyl ester (Example 45-(1); 44.9 mg, 0.071 mmol) in dichloromethane (2 mL), and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the target compound as a colorless oil (20 mg, 48%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d8f8d80c94cc4dcf9c77d6087ce88fa2
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935688B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes