Potassium Carbonate → HCID 86709754, compound

HRID 1400292Notes

Reaction equation

HRID 1400292 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].CCCCCC.C(OCC)(=O)C>CC(C)=O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 110949481-fluoronaphthalen-2-ol2×HCID 21226206Ethyl acetate hexane

Product 1

HCID 86709754HCID 86709754, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-fluoronaphthalen-2-ol (0.162 g, 1.0 mmol) and K2CO3 (0.300 g, 2.0 mmol) in acetone was added tert-butyl (2-bromoethyl)carbamate (0.336 g, 1.5 mmol). The resulting mixture was heated at reflux overnight. After TLC control (n-hexane/ethyl acetate 6:4) showed the disappearance of 1-fluoronaphthalen-2-ol, solvent was evaporated in vacuo and the residue was dissolved in 15 mL of ethyl acetate and washed with water (3×5 mL), brine (10 mL) and dried over Na2SO4. The evaporation of solvent afforded tert-butyl {2-[(1-fluoronaphthalen-2-yl)oxy]ethyl}carbamate as a white solid (65% yield) which was used without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customwas evaporated in vacuo
  4. dissolutionthe residue was dissolved in 15 mL of ethyl acetate
  5. washwashed with water (3×5 mL), brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. customThe evaporation of solvent

Sources & evidence

ORD record
ord-060728d78dd34988bc3389efd60f68d4
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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