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

HRID 514634Notes

Reaction equation

HRID 514634 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH2:16][OH:17])([CH2:14][OH:15])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]12(CS(O)(=O)=O)C(C)(C)C(C[CH2:24]1)C[C:19]2=O.C(N(CC)CC)C>CC(C)=O>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1([CH2:14][OH:15])[CH2:16][O:17][C:18]([CH3:24])([CH3:19])[O:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 537962344-Benzyloxy-2,2-dihydroxymethylbutanol

Product 1

HCID 903003655-Benzyloxyethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxaneYield 164%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

543 mg of the crude 4-benzyloxy-2,2-dihydroxymethylbutanol product was dissolved in 3 mL of acetone, 232 mg (1.0 mmol equivalents) of 10-camphorsulfonic acid was added thereto, and a reaction was carried out at room temperature (25° C.) overnight. After completion of the reaction, triethylamine was added dropwise, and the mixture was concentrated under vacuum. The crude product thus obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1) to give 459 mg (1.64 mmol equivalents) of 5-benzyloxyethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane.

Workup

  1. customwas carried out at room temperature
  2. custom(25° C.) overnight
  3. additionwas added dropwise
  4. concentrationthe mixture was concentrated under vacuum
  5. customThe crude product thus obtained
  6. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1)

Sources & evidence

ORD record
ord-8823c723f4fd494f804d0fb5717bd8cf
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

Loading…