Trifluoroacetic acid → 4-[2-(4-(Phenethyl)pyrid-3-yl)ethyl]benzoic Acid

HRID 1006033Notes

Reaction equation

HRID 1006033 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23]C(C)(C)C)=[O:22])=[CH:19][CH:18]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:28][CH:29]=1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22675531Tert-butyl 4-[2-(4-phenethyl-3-pyridyl)ethyl]benzoate

Product 1

HCID 226755104-[2-(4-(Phenethyl)pyrid-3-yl)ethyl]benzoic AcidYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-[2-(4-(phenethyl)pyrid-3-yl)ethyl]benzoate (0.36 g, 0.95 mmol) was dissolved in dichloromethane (5 ml) and treated with trifluoroacetic acid (0.5 ml). The reaction was stirred at ambient temperature for 5 hours, then partitioned between ethyl acetate and buffer (pH 6). The layers were separated and the aqueous layer extracted with ethyl acetate. The organic layers were combined, dried (MgSO4) and evaporated to give the title product (0.168 g) as a salt with THF.

Workup

  1. custompartitioned between ethyl acetate and buffer (pH 6)
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-96e26b70a8cd45bbb1b069c46ffe578f
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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