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

HRID 1106832Notes

Reaction equation

HRID 1106832 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-04bb1d44353f45c7b86118c687859824
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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