Water → HCID 86697170, compound

HRID 237508Notes

Reaction equation

HRID 237508 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:12]([CH2:15][CH2:16][CH2:17][OH:18])(=[O:14])=[O:13])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9].[C:19](=O)([O-])[O-].[Cs+].[Cs+].IC.O>C(#N)C>[CH3:19][O:18][CH2:17][CH2:16][CH2:15][S:12]([C:4]1[CH:5]=[C:6]([CH3:11])[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1)(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86697169HCID 86697169, compound

Product 1

HCID 86697170HCID 86697170, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(3,5-Dimethyl-4-nitro-benzenesulfonyl)-propan-1-ol (1.4 g) is dissolved in 20 mL of acetonitrile, cesium carbonate (3.34 g) and iodometane (638 mL) are added and the reaction mixture is stirred at room temperature overnight. Water is added and the reaction mixture is extracted with ethyl ether. The organic phase is separated, dried over sodium sulfate and concentrated under vacuum. The residue is chromatographed on silica gel (hexane/ethyl acetate 100:0→50.50) to give the title compound. Yield: 1 g.

Workup

  1. extractionthe reaction mixture is extracted with ethyl ether
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue is chromatographed on silica gel (hexane/ethyl acetate 100:0→50.50)

Sources & evidence

ORD record
ord-24fbd64bf805405fad8074006e238051
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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