Chloromethyl Methyl Ether → HCID 21942282, compound

HRID 2216347Notes

Reaction equation

HRID 2216347 reaction equation
[CH2:1]([C:8]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]([I:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][CH2:18]Cl.[H-].[Na+]>O1CCCC1>[CH2:1]([C:8]1[C:13]([O:14][CH2:16][O:17][CH3:18])=[CH:12][CH:11]=[C:10]([I:15])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride2×HCID 21942311HCID 21942311, compound

Product 1

HCID 21942282HCID 21942282, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

12 g of 2-benzyl-3-hydroxy-6-iodopyridine was dissolved in 50 ml of tetrahydrofuran and 3.8 ml of chloromethyl methyl ether was added thereto. While stirring in an ice bath, 2 g of 60% oily sodium hydride was portionwise added to the mixture. After the addition of sodium hydride, the refrigerant was removed and the mixture was stirred at room temperature for 2.5 hours. Thereafter, in an ice bath, ice water was portionwise added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed and the residue was purified by silica gel column chromatography (15% ethyl acetate/hexane), to give 13 g of the title compound.

Workup

  1. customthe refrigerant was removed
  2. stirringthe mixture was stirred at room temperature for 2.5 hours
  3. additionThereafter, in an ice bath, ice water was portionwise added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. customthe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8f79845919994544bd4cf117d7169999
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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