Isopropanol → HCID 12149034, compound

HRID 1611604Notes

Reaction equation

HRID 1611604 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:27]=[CH:26][S:25][C:24]=1[CH:28]=[O:29])([O-:16])=[O:15].C(O)(C)C>CC(C)=O>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:27]=[CH:26][S:25][C:24]=1[C:28]([OH:3])=[O:29])([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 818845HCID 818845, compoundHCID 131709961Jones' reagent

Product 1

HCID 12149034HCID 12149034, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8N Jones' reagent (ca. 30 ml) was added dropwise to a solution of 3-(2-nitrophenyl)-thiophen-2-aldehyde (8) (4.4 g, 3.1 mmol) in 32 ml of acetone, until an orange colour persisted. The mixture was left at room temperature for 18 hrs with stirring. Isopropanol (20 ml) was added to remove the excess Jones' reagent and the mixture was then filtered, the organic solvents were removed under vacuum and extracted with ethyl acetate (4×100 ml). The combined organic layer was washed with a saturated solution of NaCl, dried (Na2SO4), and evaporated under reduced pressure. The mixture was then chromatographed using 95/5 chloroform/methanol, thus giving the compound (9) (3.6 g, 66% yield).

Workup

  1. customto remove the excess Jones' reagent
  2. filtrationthe mixture was then filtered
  3. customthe organic solvents were removed under vacuum
  4. extractionextracted with ethyl acetate (4×100 ml)
  5. washThe combined organic layer was washed with a saturated solution of NaCl
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customThe mixture was then chromatographed

Sources & evidence

ORD record
ord-a602185aa96c46979b05473374a9b877
Source dataset
uspto-grants-2006_01
Patent number
US06989388B2

Reaction notes

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