Dimethylformamide → Dibenzyl ether

HRID 1248012Notes

Reaction equation

HRID 1248012 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl-].[NH4+].CN([CH:16]=[O:17])C>>[CH2:3]([O:17][CH2:16][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

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 7657Dibenzyl ether

Conditions

Temperature
25 °C

Procedure

To a slurry of 1.44 g of prewashed sodium hydride (50% dispersion in mineral oil, 27.0 mmole, 1.6 eq.) in 20 ml of dry DMF at 0° C. was added a solution of 3.85 g title A (5) alcohol (27.0 mmole) in 10 ml DMF. The mixture was stirred at 25° C. for 15 minutes, cooled to 0° C. and then 4.3 g of benzylbromide (27.0 mmole, 1.0 eq.) was added. After stirring for 30 minutes at 25° C., the reaction mixture was poured into 300 ml of a saturated aqueous ammonium chloride solution and extracted with three 100 ml of water, dried over anhydrous MgSO4 and concentrated. The residue was purified on an LPS-1 silica gel column, eluting with 10% EtOAc/hexanes to give 4.5 g of title benzylether as a yellow oil.

Workup

  1. temperaturecooled to 0° C.
  2. stirringAfter stirring for 30 minutes at 25° C.
  3. extractionextracted with three 100 ml of water
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on an LPS-1 silica gel column
  7. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-9da2b2d8485a486484e77b5f087b46af
Source dataset
uspto-grants-1985_06
Patent number
US04521539

Reaction notes

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