Chloromethyl Methyl Ether → HCID 66738421, compound

HRID 561001Notes

Reaction equation

HRID 561001 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:11][O:12][CH2:13]Cl>CN(C)C=O.C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:11][O:12][CH3:13])=[CH:6][N:7]=1

Participants

7

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 27631086-Fluoropyridin-3-ol

Product 1

HCID 66738421HCID 66738421, compoundYield 109.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 6-fluoro-pyridin-3-ol (3.5 g, 30.95 mmol) to a suspension of sodium hydride (1.49 g, 37.14 mmol) in dimethylformamide (20 mL). Stir the mixture for 1 hour. Add chloromethyl methyl ether (2 g, 25.0 mmol). Stir the mixture at room temperature overnight. Dilute the mixture with ethyl acetate and water. Wash the organic layer with water and saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to brown oil. Purify by column chromatography (10% ethyl acetate in hexane) to afford the title compound (4.30 g, 88.4%) as yellow oil. 1H NMR (400 MHz, CDCl3) δ 3.48 (s, 3H), 5.15 (s, 2H), 6.85 (dd, J=3.6 Hz, J=8.8 Hz, 1H), 7.47 (m, 1H), 7.96 (m, 1H).

Workup

  1. stirringStir the mixture at room temperature overnight
  2. washWash the organic layer with water and saturated aqueous sodium chloride
  3. dry with materialDry the mixture over sodium sulfate
  4. concentrationConcentrate the solution in vacuo to brown oil
  5. customPurify by column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f606984e12dc4f2d8689dec4e8b2107f
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

Loading…