HCID 23372556, compound → HCID 22349637, compound

HRID 260320Notes

Reaction equation

HRID 260320 reaction equation
[N+:1]([C:4]1[S:8][C:7]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])=[CH:6][CH:5]=1)([O-])=O>Cl.C(OCC)(=O)C.[OH-].[Na+]>[NH2:1][C:4]1[S:8][C:7]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 23372556HCID 23372556, compound

Product 1

HCID 22349637HCID 22349637, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of allyl 5-nitro-2-thiophenecarboxylate (3.2 g, 15 mmol) in concentrated hydrogen chloride (35 ml) were added under cooling SnCl2.H2O (10.1 g, 45 mmol). The mixture was stirred for 3.5 hours at ambient temperature, diluted with ethyl acetate and basified to pH 10 with 5N NaOH. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (3:7) to give the title compound as a yellow oil (1.94 g, 72%).

Workup

  1. washThe organic layer was washed with water
  2. dry with materiala saturated aqueous solution of sodium chloride, dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel using
  5. additiona mixture of ethyl acetate and petroleum ether (3:7)

Sources & evidence

ORD record
ord-30c2b7ed7e59453e8698289951bc8044
Source dataset
uspto-grants-1996_06
Patent number
US05527791

Reaction notes

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