Potassium Carbonate → HCID 67272423, compound

HRID 250970Notes

Reaction equation

HRID 250970 reaction equation
[O:1]([C:8]1[C:9]([CH2:14][O:15]C(=O)C)=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CO>[O:1]([C:8]1[C:9]([CH2:14][OH:15])=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 20291313HCID 20291313, compound

Product 1

HCID 67272423HCID 67272423, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of acetic acid 3-phenoxy-pyridin-2-ylmethyl ester (0.234 g, 0.96 mmol) in MeOH (10 mL) was added K2CO3 (0.264 g, 1.92 mmol) and the mixture stirred at room temperature for 2 h. The mixture was concentrated and the resultant residue was diluted with CH2Cl2 (30 mL). The organic layer was washed with saturated aqueous NaHCO3 (2×30 mL), dried (MgSO4), and concentrated to give (3-phenoxy-pyridin-2-yl)-methanol as a clear oil (0.130 g, 68%), which was used without further purification. 1H NMR (CDCl3) δ 4.26 (t, 1H, J=4.8 Hz), 4.84 (d, 2H, J=4.3 Hz), 6.97 (m, 2H), 7.18 (m, 3H), 7.37 (m, 2H), 8.32 (dd, 1H, J=2.9, 1.4 Hz).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe resultant residue was diluted with CH2Cl2 (30 mL)
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (2×30 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb114fee2f71426699edce62887f0ff3
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…