Benzyl Bromide → HCID 23295265, compound

HRID 266228Notes

Reaction equation

HRID 266228 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1.[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>COCCOC>[CH2:13]([O:1][CH2:2][CH:3]1[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanol

Product 1

HCID 23295265HCID 23295265, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 5-hydroxymethyl-2,2-dimethyl-1,3-dioxane (cf:Bates, H. A.; Farina, J.; Tong, M. J. Org. Chem. 1986, 51, 2637, 3.0 g, 20.5 mmol) in 25 mL of dry DME under argon was added via cannula to a slurry of NaH (0.740 g, 80% dispersion in oil, 24.6 mmol) in 60 mL of dry DME cooled to 0° C. The resulting grey slurry was stirred at room temperature for 0.5 h, then recooled to 0° C., and treated with a solution of benzylbromide (4.56 g, 26.7 mmol) in 20 mL of DME. The reaction mixture was stirred at room temperature (rt) overnight and then quenched with 100 ml of H2O. The aqueous layer was separated and extracted with two portions of ethyl acetate. The combined organic layers were then washed with saturated sodium chloride solution, dried over MgSO4, filtered, and concentrated to provide a yellow oil. Purification by column chromatography on silica gel (ethyl acetate/hexane) afforded 3.51 g (72%) of 5-benzyloxymethyl-2,2-dimethyl-1,3-dioxane as a clear colorless liquid.

Workup

  1. customrecooled to 0° C.
  2. stirringThe reaction mixture was stirred at room temperature (rt) overnight
  3. customquenched with 100 ml of H2O
  4. customThe aqueous layer was separated
  5. extractionextracted with two portions of ethyl acetate
  6. washThe combined organic layers were then washed with saturated sodium chloride solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto provide a yellow oil
  11. customPurification by column chromatography on silica gel (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-185ef52f90bb49ce97893123e49c77c5
Source dataset
uspto-grants-1997_07
Patent number
US05650510

Reaction notes

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