Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 59218409, compound

HRID 2246686Notes

Reaction equation

HRID 2246686 reaction equation
[C:1]1([CH2:7]/[CH:8]=[CH:9]/[C@H:10]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C3CCCCO3)=[CH:19][CH:18]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCO>[OH:23][C:20]1[CH:19]=[CH:18][C:17]([C@@H:10](/[CH:9]=[CH:8]/[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 59218387HCID 59218387, compound

Product 1

HCID 59218409HCID 59218409, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 83.5 (405.8 mg, 1.03 mmol, MW 394.50) in EtOH (11 mL) at 23° C. was added PPTS (catalytic). Stirring was continued for 16 hours. The reaction was concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated providing a colorless oil. The desired product was contaminated (˜5%) with a further olefinic product (believed to contain a terminal double bond) and was used without further purification.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes)
  3. additionFractions containing the desired product
  4. concentrationconcentrated
  5. customproviding a colorless oil

Sources & evidence

ORD record
ord-1f1e0046208c4c3fb22fef6ff884ba8e
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

Loading…