Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 57672410, compound

HRID 2101771Notes

Reaction equation

HRID 2101771 reaction equation
[CH3:1][C:2](=[CH2:23])[CH:3]([C:10]1[CH:15]=[CH:14][C:13]([O:16]C2CCCCO2)=[CH:12][CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCO>[OH:16][C:13]1[CH:12]=[CH:11][C:10]([CH:3]([C:2]([CH3:23])=[CH2:1])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57672413HCID 57672413, compound

Product 1

HCID 57672410HCID 57672410, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 15.2 (0.30 g, 0.90 mmol) in EtOH (100 mL) at room temperature was added PPTS (0.20 g, 0.90 mmol). The resulting solution was stirred for 16 hours and then concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes) to give 15.3 (0.220 g, 100%) as a clear oil. MS ESI (pos.) m/e: 257.1 (M+Na)+, 252.1 (M+H2O)+, 235.1(M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5fb69f97e9a24cb5be3cb0668ff2cadf
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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