Chloromethyl Methyl Ether → HCID 66738421, compound

HRID 1640889Notes

Reaction equation

HRID 1640889 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=O)C.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, 37.1 mmol) in DMF (20 mL). Stir the mixture for 1 h. Add chloromethyl methyl ether (2 g, 25.0 mmol). Stir the mixture at RT overnight. Dilute the mixture with ethyl acetate and water. Wash the organic layer with water and aqueous saturated sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (10% ethyl acetate in hexane) to afford the title compound (4.30 g, 88%) 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 RT overnight
  2. washWash the organic layer with water and aqueous saturated sodium chloride
  3. dry with materialDry the mixture over sodium sulfate
  4. concentrationConcentrate the solution in vacuo to a brown oil
  5. customPurify by column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4e6af8e7b5884352a6541f13ea1b4795
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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