Hexane → 1-TOSYL-1H-PYRROLE-3-CARBALDEHYDE

HRID 389008Notes

Reaction equation

HRID 389008 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.CCCCCC.C(OCC)(=O)C>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 11253747HCID 11253747, compound

Product 1

HCID 103773671-TOSYL-1H-PYRROLE-3-CARBALDEHYDEYield 51%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Manganese dioxide (100 g) was added to the solution of 11 (14.3 g, 0.057 mol) in 250 mL chloroform and the mixture was refluxed for 12 h. The mixture was then filtered and the filtrate was concentrated under vacuum to afford a yellow oil which subjected to flash chromatography (silica gel, hexane:ethyl acetate=2:1) to afford 12 as a white solid (7.2 g, 51%). 1H NMR (CDCl3, δ/ppm), 9.97 (s, 1H), 7.81 (m, 2H), 7.63 (m, 1H), 7.34 (d, 2H), 7.16 (m, 1H), 6.40 (t, 1H), 2.42 (s, 3H).

Workup

  1. temperaturethe mixture was refluxed for 12 h
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. customto afford a yellow oil which

Sources & evidence

ORD record
ord-8c0846e036f9474ab161b03072f890c2
Source dataset
uspto-grants-2013_02
Patent number
US08378058B2

Reaction notes

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