Methanesulfonic Acid → HCID 20770862, compound

HRID 1296069Notes

Reaction equation

HRID 1296069 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5](=O)[CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1.[CH3:18]S(O)(=O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[C:13]2[CH:12]=[C:11]([CH3:18])[C:10]([O:14][CH3:15])=[CH:9][C:8]=2[S:7][CH:6]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 20766005HCID 20766005, compound

Product 1

HCID 20770862HCID 20770862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 78A from the preceding step (8.6 g, 32 mmol) in 30 mL of dichloromethane was added dropwise to 30 mL of methanesulfonic acid stirred under N2 at icebath temperature. The mixture was allowed to warn gradually to room temperature. After an hour 200 mL of icewater was cautiously added (vigorous reaction!), then the mixture was partitioned between a total of 300 mL of water and 350–400 mL of dichloro-methane. The organic layer was drawn off and washed with water, then 0.5M aq NaHCO3, and dried over MgSO4. The solvent was removed in vacuo, and the residue dissolved in a minimum of CHCl3/EtOAc (24:1) and passed slowly through a column of silica gel, eluting with several column volumes of the same solvent. The effluent was stripped of solvent in vacuo to leave the title compound as a clear amber syrup, contaminated with the other possible regio-isomer, but of sufficient purity for the next step.

Workup

  1. customto warn gradually to room temperature
  2. additionAfter an hour 200 mL of icewater was cautiously added
  3. custom(vigorous reaction!)
  4. customthe mixture was partitioned between a total of 300 mL of water and 350–400 mL of dichloro-methane
  5. washwashed with water
  6. dry with material0.5M aq NaHCO3, and dried over MgSO4
  7. customThe solvent was removed in vacuo
  8. dissolutionthe residue dissolved in a minimum of CHCl3/EtOAc (24:1)
  9. washeluting with several column volumes of the same solvent

Sources & evidence

ORD record
ord-4753dd608021437cbef4bd0acca1c201
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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