Iodoethane → (3-Ethoxy-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methanol

HRID 1666437Notes

Reaction equation

HRID 1666437 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:20])[CH:6]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)[CH:8]=1.I[CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[CH2:22]([O:20][C:5]1[CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][N:11]=2)[CH:6]=1)[CH3:23]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 66876260Benzenemethanol, 3-hydroxy-5-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-

Product 1

HCID 66876312(3-Ethoxy-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methanolYield 70.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-(Hydroxymethyl)-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenol from Step 1 (460 mg, 1.61 mmol), in acetone (10 mL), was treated with 1-iodoethane (0.143 mL, 1.77 mmol), potassium carbonate (279 mg, 2.02 mmol) and 18-crown-6 (85 mg, 0.323 mmol). The mixture was heated to reflux for 16 h, cooled to room temperature and concentrated in vacuo. The residue was purified by silica gel chromatography (0-30%, EtOAc:heptane) to afford the title compound (357 mg, 70% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (0-30%, EtOAc:heptane)

Sources & evidence

ORD record
ord-7f47cf31d05542e4b354c435277825a8
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

Loading…