Triethylamine → 5-Bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane

HRID 514615Notes

Reaction equation

HRID 514615 reaction equation
[Br:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[C:10]12(CS(O)(=O)=O)C(C)(C)C(C[CH2:16]1)C[C:11]2=O.C(N(CC)CC)C>CC(C)=O>[Br:1][CH2:2][C:3]1([CH2:8][OH:9])[CH2:6][O:7][C:10]([CH3:16])([CH3:11])[O:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 879541,3-Propanediol, 2-(bromomethyl)-2-(hydroxymethyl)-

Product 1

HCID 581652605-Bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxaneYield 159.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

423 mg (2.13 mmol equivalents) of 2-bromomethyl-2-hydroxymethyl-1,3-propanediol was dissolved in 1.0 mL of acetone, 247 mg (1.07 mmol equivalents) of 10-camphorsulfonic acid was added thereto, and the mixture was stirred at room temperature (25° C.) for 2 days. After completion of the reaction, triethylamine was added, the solvent was removed by distillation, and the obtained crude product was then purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=3/1) to give 409 mg (1.71 mmol equivalents) of 5-bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane.

Workup

  1. additionwas added
  2. customthe solvent was removed by distillation
  3. customthe obtained crude product
  4. customwas then purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=3/1)

Sources & evidence

ORD record
ord-fc3953eb11924255a1cd5085cdbb9ce4
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

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