Chloromethyl Methyl Ether → HCID 59655787, compound

HRID 2054351Notes

Reaction equation

HRID 2054351 reaction equation
[N:1]1[C:14]2[N:8]3[C:9](=[O:13])[NH:10][CH:11]=[CH:12][C:7]3=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:17](Cl)[O:18][CH3:19]>CN(C=O)C>[CH3:17][O:18][CH2:19][N:10]1[CH:11]=[CH:12][C:7]2=[CH:6][C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:14]=3[N:8]2[C:9]1=[O:13]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 11401184HCID 11401184, compound

Product 1

HCID 59655787HCID 59655787, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 11a (250 mg, 1.4 mmol) in DMF (10 ml), NaH (65 mg, 1.6 mmol) was added. The mixture was stirred for 10 min. and MOMCl (103 μl, 1.4 mmol) was dropwise added. The mixture was stirred at 0° C. for 1 h and quenched with water (1 ml). The solvent was evaporated and the residue dissolved in CH2Cl2. The organic solution was washed with aq. Na2CO3, evaporated and purified by flash column chromatography. Elution with CH2Cl2/MeOH (95/5) gave 12 (267 mg, 87%) as a white solid.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at 0° C. for 1 h
  3. customquenched with water (1 ml)
  4. customThe solvent was evaporated
  5. dissolutionthe residue dissolved in CH2Cl2
  6. washThe organic solution was washed with aq. Na2CO3
  7. customevaporated
  8. custompurified by flash column chromatography
  9. washElution with CH2Cl2/MeOH (95/5)

Sources & evidence

ORD record
ord-7336dc95e6554a54ad5734f088436da2
Source dataset
uspto-grants-2008_02
Patent number
US07329666B2

Reaction notes

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