Triethylsilane → HCID 11186386, compound

HRID 1633724Notes

Reaction equation

HRID 1633724 reaction equation
O[CH:2]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:15]=1[CH3:23])[C:3]1[N:4]=[CH:5][N:6]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:7]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:13][N:11]([CH3:12])[S:8]([N:6]1[CH:7]=[C:3]([CH2:2][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:15]=2[CH3:23])[N:4]=[CH:5]1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 18679783HCID 18679783, compound

Product 1

HCID 11186386HCID 11186386, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Example 28B in trifluoroacetic acid (15 mL) was treated with triethyl silane (1.5 mL), heated to reflux for 16 hours, cooled, concentrated, tritrated with hexanes, treated with sodium bicarbonate solution and extracted with dichloromethane (×2). The combined dichloromethane layers were dried (MgSO4), filtered and concentrated. Purification of the residue on silica gel with ether provided the desired product enriched in the 3-nitro isomer.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. additiontreated with sodium bicarbonate solution
  6. extractionextracted with dichloromethane (×2)
  7. dry with materialThe combined dichloromethane layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the residue on silica gel with ether

Sources & evidence

ORD record
ord-b950813f40114cd08e166a24c449f33a
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

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