p-Toluenesulfonic acid → HCID 69159246, compound

HRID 1294374Notes

Reaction equation

HRID 1294374 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:16])[CH:9]([OH:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.CO[C:19](OC)([CH3:21])[CH3:20].CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:16][C:19]([CH3:21])([CH3:20])[O:15][CH:9]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 69159245HCID 69159245, compound

Product 1

HCID 69159246HCID 69159246, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of diol from step 1 (1 eq) in acetone (0.2M), dimethoxypropane (8 eq) and pTsOH (0.05 eq) was stirred at rt for 4 h. The solvent was evaporated, the residue dissolved in EtOAc and washed with aqueous NaHCO3 sol. The organic extract was washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (hexane:EtOAc, 95:5 to 85:15) afforded the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with aqueous NaHCO3 sol. The
  4. extractionorganic extract
  5. washwas washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2467a8ff02f144e2829e04306d0da170
Source dataset
uspto-grants-2007_07
Patent number
US07238706B2

Reaction notes

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