Water → HCID 19900760, compound

HRID 1029765Notes

Reaction equation

HRID 1029765 reaction equation
[C:1]([C:5]1([C:13]2[S:17][C:16]([S:18]([CH2:21][N+:22]([O-:24])=[O:23])(=[O:20])=[O:19])=[CH:15][CH:14]=2)OCC(C)(C)C[O:6]1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.O>C(O)C>[CH3:2][C:1]([CH3:4])([CH3:3])[C:5]([C:13]1[S:17][C:16]([S:18]([CH2:21][N+:22]([O-:24])=[O:23])(=[O:20])=[O:19])=[CH:15][CH:14]=1)=[O:6]

Participants

5

Reactant 3

HCID 962Water2×HCID 6422Trifluoroacetic acidHCID 19900772HCID 19900772, compound

Product 1

HCID 19900760HCID 19900760, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-t-butyl-5,5-dimethyl-2-[2-(nitromethylsulphonyl)thien-5-yl]-1,3-dioxane (A) (1.47 g), trifluoroacetic acid (15 ml), and water (1.5 ml) was stirred for 45 minutes at 60° C. The reaction mixture was poured into water (50 ml), and extracted with ether (2×50 ml). The combined ether extracts were washed with saturated aqueous sodium hydrogen carbonate solution (20 ml), water (3×20 ml), and then dried (MgSO4). The solvent was removed by evaporation to give 2-(2,2-dimethylpropionyl)-5-(nitromethylsulphonyl)thiophene as a white solid (0.605 g, 54% yield), m.p. 98°-99° C. (after recrystallisation from aqueous ethanol); MMR (250 MHz): 1.42(s, 9H), 5.72(s, 2H), 7.78(d, 1H), 7.82(d, 1H); m/e (electron impact) 292 (M+H)+ ; microanalysis, found: C,41.3, H.4.5, N,4.7%; C10H13NO5S2 requires: C,41.2, H,4.5, N,4.8%.

Workup

  1. extractionextracted with ether (2×50 ml)
  2. washThe combined ether extracts were washed with saturated aqueous sodium hydrogen carbonate solution (20 ml), water (3×20 ml)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed by evaporation
  5. customto give

Sources & evidence

ORD record
ord-aa1cd54fe5ed45a9a6fea470b41c5df8
Source dataset
uspto-grants-1992_04
Patent number
US05102905

Reaction notes

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