Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 54389298, compound

HRID 2225789Notes

Reaction equation

HRID 2225789 reaction equation
[CH3:1][C:2]1[C:3]([C:17]#[C:18][CH2:19][O:20]C2CCCCO2)=[C:4]([CH2:8][O:9][C:10](=[O:16])[C:11]([CH3:15])([CH3:14])[CH2:12][CH3:13])[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:20][CH2:19][C:18]#[C:17][C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:8][O:9][C:10](=[O:16])[C:11]([CH3:15])([CH3:14])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19004289HCID 19004289, compound

Product 1

HCID 54389298HCID 54389298, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A solution of rac-2,2-dimethylbutanoic acid [3-methyl-2-[3-(2-tetrahydropyranyloxy)-1-propynyl]phenyl]methyl ester (2 g) and pyridinium p-toluenesulfonate in ethanol (30 mL) was stirred and heated in an oil bath maintained at 55° C. for 3.5 hours then the solvent was evaporated and the residue triturated with diethyl ether. After a small amount of pyridinium p-toluenesulfonate was Filtered off, the filtrate was evaporated and the residual oil was purified by HPLC (diethyl ether-hexane; 1:3) to furnish 1.38 g of 2,2-dimethylbutanoic acid [2-(3-hydroxy-1-propynyl)-3-methylphenyl]methyl ester as a colorless oil.

Workup

  1. temperatureheated in an oil bath
  2. customthe solvent was evaporated
  3. customthe residue triturated with diethyl ether
  4. filtrationAfter a small amount of pyridinium p-toluenesulfonate was Filtered off
  5. customthe filtrate was evaporated
  6. customthe residual oil was purified by HPLC (diethyl ether-hexane; 1:3)

Sources & evidence

ORD record
ord-3464262641e741eea0db53f018d6c34c
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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