Methanesulfonic Acid → HCID 22459084, compound

HRID 2185061Notes

Reaction equation

HRID 2185061 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH2:7][C:8](=O)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CS(O)(=O)=O.[OH-].[Na+].C(OC)(C)(C)C>C(Cl)Cl>[C:11]1([CH2:10][CH2:9][C:8]2[C:18]3[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[O:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 22459131HCID 22459131, compound

Product 1

HCID 22459084HCID 22459084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product from Step A (2.368 grams), dissolved in dry CH2Cl2 (25 mL) was added dropwise to a −10° C. CH2Cl2 solution (10 mL) of methanesulfonic acid (5.68 mL). The reaction was warmed to ambient temperature and stirred for 30 minutes. 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 (step gradient; 4:1 hex/CH2Cl2 to 1:1 hex/CH2Cl2) gave the title compound as a clear oil.

Workup

  1. additionwas added dropwise to a −10° C
  2. dry with materialThe organic was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationConcentration and chromatography over silica gel (step gradient; 4:1 hex/CH2Cl2 to 1:1 hex/CH2Cl2)

Sources & evidence

ORD record
ord-e48b986009174b1a82ee424714be7618
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

Loading…