Dimethylformamide → Dibenzyl ether

HRID 2056953Notes

Reaction equation

HRID 2056953 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN([CH:14]=[O:15])C>>[CH2:3]([O:15][CH2:14][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 7657Dibenzyl ether

Procedure

To a solution of the above alcohol (430 mg, 3.0 mmol) in DMF (10 mL) was added NaH (144 mg of a 60% dispersion in mineral oil, 3.60 mmol) and the mixture was then cooled in an ice bath. Benzyl bromide (437 uL, 3.60 mmol) was then added and the mixture was stirred at room temperature for 3 h. After normal aqueous work-up and short column chromatographic purification, 600 mg of desired benzyl ether was obtained.

Workup

  1. temperaturewas then cooled in an ice bath
  2. customAfter normal aqueous work-up and short column chromatographic purification

Sources & evidence

ORD record
ord-5fcf3e72308241e3b26bd86094ceeeda
Source dataset
uspto-grants-2008_02
Patent number
US07335657B2

Reaction notes

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