Methanesulfonic Acid → HCID 22458950, compound

HRID 2185047Notes

Reaction equation

HRID 2185047 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:10][C:11](=O)[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:7][CH:8]=1.CS(O)(=O)=O.[OH-].[Na+].C(OC)(C)(C)C>C(Cl)Cl>[C:14]1([CH2:13][CH2:12][C:11]2[C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[S:9][CH:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 22459070HCID 22459070, compound

Product 1

HCID 22458950HCID 22458950, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product from Step C (8.495 grams), dissolved in dry CH2Cl2 (85 mL) was added dropwise to a 0° C. CH2Cl2 solution (34mL) of methanesulfonic acid (17 mL). The reaction was kept at 0° C. for 20 minutes, then briefly warmed to ambient temperature. The reaction was rapidly poured into a vigorously stirred cold mixture of excess 5N NaOH and methyl tert-butyl ether. The organic was dried over magnesium sulfate and filtered. Concentration and chromatography over silica gel (5:1 hex/CH2Cl2) gave the title compound as a clear oil.

Workup

  1. additionwas added dropwise to a 0° C
  2. dry with materialThe organic was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationConcentration and chromatography over silica gel (5:1 hex/CH2Cl2)

Sources & evidence

ORD record
ord-75abd7fe3b4b42c68344fbd3707c8c11
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

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