Dimethylformamide → 5-Benzyloxy-1-methoxy-pentane

HRID 1822880Notes

Reaction equation

HRID 1822880 reaction equation
[H-].[Na+].CN(C)[CH:5]=[O:6].[CH2:8]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CI>O>[CH2:8]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:6][CH3:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 2211945-(Benzyloxy)pentan-1-ol

Product 1

HCID 221705565-Benzyloxy-1-methoxy-pentaneYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.6 g (0.039 mol) of 55% sodium hydride in oil were added to 50 ml of dimethylformamide under stirring at room temperature. 5 ml (0.026 mol) of 5-benzyloxy-1-pentanol and 2.43 ml (0.039 mol) of methyl iodide were then added successively. After a night the excess of sodium hydride was decomposed with water and the solvent evaporated under vacuum. The residue was redissolved with methylene chloride and washed with water. The organic layer was finally dried over anhydrous sodium sulfate and evaporated to give 3.5 g (70% yield) of the title compound.

Workup

  1. customthe solvent evaporated under vacuum
  2. dissolutionThe residue was redissolved with methylene chloride
  3. washwashed with water
  4. dry with materialThe organic layer was finally dried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2f902dd068264514872be095c1a52f61
Source dataset
uspto-grants-2006_05
Patent number
US07037929B1

Reaction notes

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