Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 15489032, compound

HRID 351106Notes

Reaction equation

HRID 351106 reaction equation
[CH3:1][O:2][C:3](=[O:48])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C@@H:14]([O:15]C2CCCCO2)[CH2:13][C@@H:12]([O:22]C2CCCCO2)[C@@H:11]1/[CH:29]=[CH:30]/[C@@H:31]([O:41]C1CCCCO1)[CH2:32][CH2:33][C:34]1[S:35][C:36]([CH3:40])=[C:37]([Br:39])[CH:38]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[CH3:1][O:2][C:3](=[O:48])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C@@H:14]([OH:15])[CH2:13][C@@H:12]([OH:22])[C@@H:11]1/[CH:29]=[CH:30]/[C@@H:31]([OH:41])[CH2:32][CH2:33][C:34]1[S:35][C:36]([CH3:40])=[C:37]([Br:39])[CH:38]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 71196551HCID 71196551, compound

Product 1

HCID 15489032HCID 15489032, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the crude ester (2) in methanol (16 mL) was treated with pyridinium p-toluenesulfonate (2.625 g, 10.4 mmol). After 21 h, the solvent was evaporated in vacuo and the residue purified by flash chromatography on silica gel (90% ethyl acetate/hexanes→95%) to give 3 (3.453 g, 6.9 mmol, 86% for the two steps).

Workup

  1. customthe solvent was evaporated in vacuo
  2. customthe residue purified by flash chromatography on silica gel (90% ethyl acetate/hexanes→95%)
  3. customto give 3 (3.453 g, 6.9 mmol, 86% for the two steps)

Sources & evidence

ORD record
ord-2bae7d246e1d4625b8c8a3ddf462c8c9
Source dataset
uspto-grants-2007_02
Patent number
US07183310B2

Reaction notes

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