p-Toluenesulfonic acid → HCID 54500514, compound

HRID 1657749Notes

Reaction equation

HRID 1657749 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][OH:13])[CH:3]=1.[C:14]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:15][CH2:16][C:17]([CH3:19])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C1C=CC=CC=1>[CH2:22]([O:21][C:14](=[O:20])[CH2:15][CH2:16][C:17]1([CH3:19])[C:3]2=[C:2]([CH3:1])[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]2[CH2:11][CH2:12][O:13]1)[CH3:23]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 10883Ethyl levulinateHCID 122267423-Methylindole-1-ethanol

Product 1

HCID 54500514HCID 54500514, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of the intermediate of formula III, 3-methylindole-1-ethanol (29.7 g., 0.17 mole), described in Example 1, ethyl levulinate (26.96 g., 0.187 mole) and p-toluenesulfonic acid (2.25 g.) in dry benzene (650 ml.) is refluxed with stirring for 12 hr. with hydrated alkalialuminum silicate (Molecular Sieves No. 4). The benzene solution is washed with 5% aqueous NaHCO3, followed by water. Concentrations of the solution gave a residue, which is passed through a silica gel column using 15% ethyl acetate in benzene to afford the ester, 3,4-dihydro-1,10-dimethyl1H-1,4-oxazino[4,3-a]indole-1-propionic acid ethyl ester, as an oil, γmaxCHCl5 1730 cm-1.

Workup

  1. temperatureis refluxed
  2. washThe benzene solution is washed with 5% aqueous NaHCO3
  3. customConcentrations of the solution gave a residue, which

Sources & evidence

ORD record
ord-f26c45cdb78349c0b3187b79a8a6999a
Source dataset
uspto-grants-1976_06
Patent number
US03962236

Reaction notes

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