Nitromethane → HCID 57237145, compound

HRID 982108Notes

Reaction equation

HRID 982108 reaction equation
O[CH:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:13][O:14][CH3:15])[C:6]=2[CH2:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:3]1.C([O-])(=O)C.[NH4+].[N+:27]([CH3:30])([O-:29])=[O:28]>>[CH3:15][O:14][CH2:13][O:12][C:11]1[C:6]2[CH2:5][C@@H:4]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:3][C@@H:2]([CH2:30][N+:27]([O-:29])=[O:28])[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 15711862HCID 15711862, compound2×

Product 1

HCID 57237145HCID 57237145, compoundYield 11%

Procedure

A solution of 1.81 g (6.3 mmol) of 3,4-dihydro-1-hydroxy-5-methoxymethoxy-3-phenyl-1H-2-benzopyran (the product of Step 2 of Example 89) and 488 mg (1.8 mmol) of ammonium acetate in 30 mL of nitromethane was heated at reflux for 3 days and then concentrated in vacuo, the concentrate was poured into 30 mL of a 1M aqueous hydrochloric acid solution and the cloudy mixture was extracted with 2×150 mL of ethyl acetate. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel eluted with hexane/diethyl ether (8:1 v/v) to give 230 mg (11% yield) of the title compound.

Workup

  1. temperatureat reflux for 3 days
  2. concentrationconcentrated in vacuo
  3. additionthe concentrate was poured into 30 mL of a 1M aqueous hydrochloric acid solution
  4. extractionthe cloudy mixture was extracted with 2×150 mL of ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified on silica gel
  11. washeluted with hexane/diethyl ether (8:1 v/v)

Sources & evidence

ORD record
ord-5f716c36984d4ee58e0ec69c3468d479
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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