p-Toluenesulfonic acid → HCID 67215909, compound

HRID 468598Notes

Reaction equation

HRID 468598 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][CH2:11][C:12]([O:14][CH2:15][CH2:16][O:17][CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:13].CC1C=CC(S(O)(=O)=O)=CC=1>CO>[OH:7][CH2:8][CH2:9][O:10][CH2:11][C:12]([O:14][CH2:15][CH2:16][O:17][CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])=[O:13]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67226568HCID 67226568, compound

Product 1

HCID 67215909HCID 67215909, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of THP-protected hydroxy ester 5 (1 g, 2.53 mmol) in methanol (35 ml) was added p-TsOH (30 mg, 1 mg/ml). The reaction mixture was stirred at room temperature for 1 hr, concentrated and diluted with EtOAc. Organic layer was washed twice with NaHCO3 and water, dried over MgSO4, filtered and concentrated. The obtained oily residue (712 mg, 90%) was used for next step without further purification.

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 oily residue (712 mg, 90%) was used for next step without further purification

Sources & evidence

ORD record
ord-8458924cb21040d6953e2516c7ec00af
Source dataset
uspto-grants-2014_01
Patent number
US08624044B2

Reaction notes

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