p-Toluenesulfonic acid → HCID 22593753, compound

HRID 1920976Notes

Reaction equation

HRID 1920976 reaction equation
[C:1]([CH2:6][S:7][C:8]1[S:9][CH:10]=[CH:11][C:12]=1[CH:13]1OCC[O:14]1)([O:3][CH2:4][CH3:5])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[C:1]([CH2:6][S:7][C:8]1[S:9][CH:10]=[CH:11][C:12]=1[CH:13]=[O:14])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 225937642-(Carboethoxymethylthio)-3-(1,3-dioxolan-2-yl)thiophene

Product 1

HCID 22593753HCID 22593753, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(carboethoxymethylthio)-3-(1,3-dioxolan-2-yl)thiophene (from step b) in acetone (200 mL) was added p-toluenesulfonic acid (761 mg, 4.0 mmole) at RT. After 18 hr the mixture was concentrated. The residue was taken up in Et2O, washed with saturated NaHCO3, H2O (2×), dried (MgSO4), and concentrated under reduced pressure to give the title compound as an oil which was sufficiently pure for use in the next step.

Workup

  1. concentrationAfter 18 hr the mixture was concentrated
  2. washwashed with saturated NaHCO3, H2O (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78a8c45d1c764682849d772eca5241db
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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