p-Toluenesulfonic acid → HCID 68316807, compound

HRID 468596Notes

Reaction equation

HRID 468596 reaction equation
C([CH:8]([O:12][CH2:13][CH2:14][O:15]C1CCCCO1)[C:9]([O-:11])=[O:10])C1C=CC=CC=1.[CH3:22][C:23]1[CH:24]=[CH:25][C:26](S(O)(=O)=O)=[CH:27][CH:28]=1>CO>[OH:15][CH2:14][CH2:13][O:12][CH2:8][C:9]([O:11][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:10]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86674056HCID 86674056, compound

Product 1

HCID 68316807HCID 68316807, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of THP-protected hydroxy ester 3 (2 g, 6.8 mmol) in methanol (80 ml) was added p-TsOH (80 mg, 1 mg/ml). The reaction mixture was stirred at room temperature for 45 nm, concentrated and diluted with EtOAc. Organic layer was washed twice with NaHCO3 and water, dried over MgSO4, filtered and concentrated. The obtained residue was either used without further purification for next step or, if needed, purified by flash chromatography on silica gel (EtOAc/pentane 1/1) to give hydroxy ester 4 as an oil.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc
  3. washOrganic layer was washed twice with NaHCO3 and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe obtained residue was either used without further purification for next step
  8. custompurified by flash chromatography on silica gel (EtOAc/pentane 1/1)

Sources & evidence

ORD record
ord-9bf0b38677ce4a43ad974e98ba1bbdbe
Source dataset
uspto-grants-2014_01
Patent number
US08624044B2

Reaction notes

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