Chloromethyl Methyl Ether → HCID 21942282, compound

HRID 1359278Notes

Reaction equation

HRID 1359278 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, followed by adding 3.8 ml of chloromethyl methyl ether. 2 g of 60% oily sodium hydride was added little by little thereto to under stirring under ice-cooling. After adding sodium hydride, the cooling medium was removed and the mixture was stirred at room temperature for 2.5 hours. Then, ice water was added thereto little by little under cooling, followed by extracting with ethyl acetate. The organic phase was further washed brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 15% ethyl acetate/hexane as an eluent for separation and purification, to give 13 g of the target compound.

Workup

  1. temperaturecooling
  2. customthe cooling medium was removed
  3. stirringthe mixture was stirred at room temperature for 2.5 hours
  4. additionThen, ice water was added
  5. temperaturelittle by little under cooling
  6. extractionby extracting with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed
  9. customfor separation and purification

Sources & evidence

ORD record
ord-27b6dc765ebd49e6a7b93f0760839363
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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