p-Toluenesulfonic acid → HCID 178442700, compound

HRID 1737156Notes

Reaction equation

HRID 1737156 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:11](=[O:12])[C:10]([OH:13])=[CH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.[CH2:14]1COCC1.N1CCCC1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27](S(O)(=O)=O)=[CH:26][CH:25]=1>C1C=CC=CC=1>[CH3:14][C:24]([CH3:25])([CH3:34])[CH2:29][CH2:28][CH:27]=[CH:26][C:9]1[C:7](=[O:8])[C:5]2[C:4]([C:11](=[O:12])[C:10]=1[OH:13])=[CH:3][CH:2]=[CH:1][CH:6]=2

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 31268PyrrolidineHCID 178516607HCID 178516607, compound2×

Product 1

HCID 178442700HCID 178442700, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The aldehyde (8.46 mmol) was coupled to lawsone following the procedure set out in Example 42 using lawsone (1.18 g),THF (20 ml), pyrrolidine (672 μl), benzene (40 ml) and p-toluenesulphonic acid (1.95 g). 391 mg of the title compound was isolated after purification.

Sources & evidence

ORD record
ord-52acfb1f88a44f609e931ae1d08f361a
Source dataset
uspto-grants-1999_10
Patent number
US05962002

Reaction notes

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