Trimethylsilyl triflate → HCID 10357417, compound

HRID 1654782Notes

Reaction equation

HRID 1654782 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[Br:13])[C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].C[Si](C)(C)[O:17][CH:18](O[Si](C)(C)C)[CH3:19].C[Si](OS(C(F)(F)F)(=O)=O)(C)C>C(Cl)Cl>[CH2:18]1[O:17][C:9]2([C:10]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[C:12]([Br:13])[CH:11]=3)[CH2:7][CH2:8]2)[O:14][CH2:19]1

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 100609406-bromo-5-nitro-2,3-dihydro-1H-inden-1-oneHCID 18183672HCID 18183672, compound

Product 1

HCID 10357417HCID 10357417, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-nitro-6-bromo-1-indanone (11.0 g, 43 mmol) and bis(trimethylsilyloxy)ethane (22.0 mL, 90 mmol) in CH2Cl2 (90 mL) at room temperature was added trimethylsilyltrifluoromethanesulfonate (100 μL). The mixture was stirred for 2 h and the homogeneous solution was quenched with saturated aqueous NaHCO3 (100 mL). The CH2Cl2 layer was separated, washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. Chromatography over silica gel, eluting with ethyl acetate:hexanes (2:5), furnished 10.2 g (79%) of the title compound as a pale yellow solid.

Workup

  1. customthe homogeneous solution was quenched with saturated aqueous NaHCO3 (100 mL)
  2. customThe CH2Cl2 layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. washChromatography over silica gel, eluting with ethyl acetate:hexanes (2:5)

Sources & evidence

ORD record
ord-5f5870a47b644ae68d7b679edc7fac00
Source dataset
uspto-grants-1995_04
Patent number
US05409944

Reaction notes

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