Methanesulfonic Acid → HCID 19745023, compound

HRID 2254395Notes

Reaction equation

HRID 2254395 reaction equation
[OH:1][N:2]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][C:5](=NO)[CH2:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].CS(O)(=O)=O>O1CCCC1>[OH:1][N:2]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][C:5]([O:28][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([O:28][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 81031-HexanolHCID 19745021HCID 19745021, compound

Product 1

HCID 19745023HCID 19745023, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.0 g (0.035 mole) 1-hydroxy-2,6-diphenyl-4-piperidone oxime, 22.0 g (0.22 moles) 1-hexanol and 7.0 g (0.073 moles) methanesulfonic acid in 250 mL tetrahydrofuran is heated at 60° C. for 12 hours. The solution is then washed three times with 10% aqueous sodium carbonate solution. The organic phase is dried over anhydrous sodium sulfate and concentrated. 3.2 g (20% yield) of the title compound is isolated as a clear oil after purification by LC (silica gel, ethyl acetate:hexane).

Workup

  1. washThe solution is then washed three times with 10% aqueous sodium carbonate solution
  2. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e809c97d79224e26b6d83e590a8938bb
Source dataset
uspto-grants-1993_08
Patent number
US05235056

Reaction notes

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