p-Toluenesulfonic acid monohydrate → HCID 13821616, compound

HRID 1905095Notes

Reaction equation

HRID 1905095 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].O.[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C=C>[O:1]=[C:2]([CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])[CH2:3][C:4]([O:6][CH2:7][CH:8]=[CH2:23])=[O:5]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 3605475HCID 3605475, compound

Product 1

HCID 13821616HCID 13821616, compound

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent

Procedure

A solution of 2.89 g (10.0 mmol) of ethyl 3-oxo-5-phthalimidopentanoate in 14 ml of allyl alcohol was heated at 80° C. in the presence of catalytic amounts of p-toluenesulphonic acid hydrate for 3 days. The solvent was then evaporated in vacuo and the residue was purified by chromatography on 170 g of silica gel (toluene:ethyl acetate 4:1). The title compound was obtained as colorless crystals, melting point: 53°-55° C., Rf: 0.40 (toluene:ethyl acetate 4:1).

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe residue was purified by chromatography on 170 g of silica gel (toluene:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-abb6cdc6c39e43e3adf93b4b10e3946d
Source dataset
uspto-grants-1989_06
Patent number
US04841042

Reaction notes

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