Trifluoroacetic acid → HCID 86703749, compound

HRID 1849862Notes

Reaction equation

HRID 1849862 reaction equation
[Cl:1][C:2]1[C:3]([O:16][CH2:17][CH:18]2[CH:23]([CH3:24])[CH2:22][CH2:21][CH2:20][CH:19]2[CH3:25])=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9]C(C)(C)C)=[O:8].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([O:16][CH2:17][CH:18]2[CH:23]([CH3:24])[CH2:22][CH2:21][CH2:20][CH:19]2[CH3:25])=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703748HCID 86703748, compound

Product 1

HCID 86703749HCID 86703749, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 5-chloro-4-((2,6-dimethylcyclohexyl)-methoxy)-2-fluorobenzoate (0.21 g, 0.58 mmol) in dichloromethane (2 mL), was added trifluoroacetic acid (2 mL). The reaction mixture was stirred at 0° C. for 1 hour and then concentrated in vacuo. The residue was purified by column chromatography (0 to 30% gradient ethyl acetate in hexanes) to afford the title compound (0.071 g, 38%): MS (ES−) m/z 315.2, 313.2 (M−1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (0 to 30% gradient ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-47a40f45700a4409bf6e0cf62ead91e3
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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