p-Toluenesulfonic acid → (S)-4-(2-(benzyloxy)ethyl)-2,2,4-trimethyl-1,3-dioxolane

HRID 332073Notes

Reaction equation

HRID 332073 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@:11]([CH3:15])([OH:14])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:18](OC)([CH3:20])[CH3:19].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][C@@:11]1([CH3:15])[CH2:12][O:13][C:18]([CH3:20])([CH3:19])[O:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 67205693(S)-4-(benzyloxy)-2-methylbutane-1,2-diol

Product 1

HCID 67204923(S)-4-(2-(benzyloxy)ethyl)-2,2,4-trimethyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of compound 2 and 2,2-dimethoxypropane in DCM was added p-TSA. After TLC monitoring showed the disappearance of the starting material, aqueous NaHCO3 solution was added and then extracted with ethyl acetate three times. The combined organic phase was washed with brine and dried (Na2SO4). The solid was filtered and the solvent was removed. The residue was purified by column chromatography to give compound 3.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationThe solid was filtered
  6. customthe solvent was removed
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-455d9117370549a3a13f2bb8baa1c950
Source dataset
uspto-grants-2014_11
Patent number
US08877796B2

Reaction notes

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