Potassium Carbonate → Naphthalen-2-ylmethyl 3,3,3-trifluoro-2,2-dimethylpropanoate

HRID 473362Notes

Reaction equation

HRID 473362 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=[O:5].Br[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4]([O:6][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 198673673,3,3-Trifluoro-2,2-dimethylpropanoic acid

Product 1

HCID 57515862Naphthalen-2-ylmethyl 3,3,3-trifluoro-2,2-dimethylpropanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 3,3,3-trifluoro-2,2-dimethylpropanoic acid (2.96 g, 19.0 mmol), 2-(bromomethyl)naphthalene (4.19 g, 19.0 mmol), and potassium carbonate (7.86 g, 56.9 mmol) in 50 ml of anhydrous DMF was stirred at 30° C. overnight. Diluted with 150 ml of EtOAc, washed with 150 ml of H2O, 2×100 ml of 1N NaOH, 2×100 ml of 1N HCl, dried (Na2SO4) and concentrated to give an oil that was purified by ISCO using EtOAc in hexanes (5%) as eluents to provide the title compound as an oil.

Workup

  1. washwashed with 150 ml of H2O, 2×100 ml of 1N NaOH, 2×100 ml of 1N HCl
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto give an oil that
  5. customwas purified by ISCO

Sources & evidence

ORD record
ord-83afe82d8b6f438aadd9e928f5c488f7
Source dataset
uspto-grants-2014_01
Patent number
US08633315B2

Reaction notes

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