p-Toluenesulfonic acid → HCID 19021020, compound

HRID 1975629Notes

Reaction equation

HRID 1975629 reaction equation
[Cl:1][C:2]1[S:6][N:5]([CH2:7][CH2:8]C=O)[C:4](=[O:11])[CH:3]=1.[CH:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C(O)C>[CH2:20]([O:19][CH:12]([O:16][CH2:17][CH3:18])[CH2:8][CH2:7][N:5]1[C:4](=[O:11])[CH:3]=[C:2]([Cl:1])[S:6]1)[CH3:21]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 31214Ethyl orthoformateHCID 19021024HCID 19021024, compound

Product 1

HCID 19021020HCID 19021020, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 5 (2.5 g, 0.013 mole), triethyl orthoformate (3.87 g, 0.026 mole) in 20 ml ethanol and p-toluenesulfonic acid (35 mg) was refluxed for 18 hours. Upon cooling, the mixture was treated with 0.2 ml of triethylamine and extracted with diethyl ether. The extract was then washed successively with NaHCO3 solution, water and brine. After drying (MgSO4), the solvent was removed in vacuo. The residual brown oil was purified by column chromatography on silica gel, using diethyl ether/hexane (4/1) as eluant. The product was obtained as a light brown oil; 2.2 g; IR (neat) 1625 cm-1 ; NMR (CDCl3) δ6.3 (s,1H); 4.6 (t,1H); 3.85 (t, 2H); 3.4-3.8 (m,4H); 2.0 (q,2H); 1.2 (t,6H).

Workup

  1. temperatureUpon cooling
  2. extractionextracted with diethyl ether
  3. washThe extract was then washed successively with NaHCO3 solution, water and brine
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customThe residual brown oil was purified by column chromatography on silica gel
  7. customThe product was obtained as a light brown oil

Sources & evidence

ORD record
ord-593c52e23c00492da22d8807fcb84bbe
Source dataset
uspto-grants-1994_02
Patent number
US05288693

Reaction notes

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