Benzyl Bromide → 2-(benzyloxymethyl)-3,4-dihydro-2H-pyran

HRID 1626014Notes

Reaction equation

HRID 1626014 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:11]([O:8][CH2:7][CH:2]1[CH2:3][CH2:4][CH:5]=[CH:6][O:1]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 955593,4-dihydro-2H-pyran-2-methanol

Product 1

HCID 40956582-(benzyloxymethyl)-3,4-dihydro-2H-pyranYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dihydro-2H-pyran-2-ylmethanol (5.0 g) was dissolved in tetrahydrofuran (100 ml). 55% Sodium hydride (2.3 g) and benzyl bromide (8.2 g) were added under ice-cooling, followed by stirring for 17 hours. A saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate and washing with brine. The organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (8.5 g) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing with brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane)

Sources & evidence

ORD record
ord-762c373a4e5c426a9c4d715d5a2ce5c0
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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