Benzyl Bromide → Benzyl glycidyl ether

HRID 970405Notes

Reaction equation

HRID 970405 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:5][O:4]1.[H-].[Na+].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C>[C:9]1([CH2:8][O:1][CH2:2][CH:3]2[CH2:5][O:4]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11164GlycidolHCID 24758Sodium hydride

Product 1

HCID 94247Benzyl glycidyl etherYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of (+/−)-2-(hydroxymethyl)oxirane (3.0 g, 40.5 mmol, Aldrich) in dry DMF (40 mL) was added sodium hydride (883 mg, 36.8 mmol, Aldrich). The reaction was stirred for 7 min when benzyl bromide (6.3 g, 36.8 mmol, Aldrich) was added. The reaction was stirred for 2 h and then quenched by the addition of water (50 mL). The reaction was extracted with EtOAc (4×50 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and conc. in vacuo to a yellow oil. The oil was purified by flash chromatography (SiO2, 5–20% EtOAc in hexanes) to yield 4.15 g of a colorless oil. MS (ESI) 164 (M+H).

Workup

  1. additionwas added
  2. customquenched by the addition of water (50 mL)
  3. extractionThe reaction was extracted with EtOAc (4×50 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customThe oil was purified by flash chromatography (SiO2, 5–20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-975be854a9204dc4af5d0e9c85aa6f0e
Source dataset
uspto-grants-2007_12
Patent number
US07312222B2

Reaction notes

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