Tetrahydrofuran → HCID 87330275, compound

HRID 1040613Notes

Reaction equation

HRID 1040613 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:12](=[CH:13][CH:14]=1)[CH:11]1[O:15][CH:7]2[CH2:8][NH:9][CH2:10]1)([O-:3])=[O:2].[CH2:16](Cl)[C:17]#[CH:18].C(=O)([O-])[O-].[K+].[K+].C1COCC1>C([O-])(O)=O.[Na+]>[N+:1]([C:4]1[CH:5]=[C:6]2[C:12](=[CH:13][CH:14]=1)[CH:11]1[O:15][CH:7]2[CH2:8][N:9]([CH2:18][C:17]#[CH:16])[CH2:10]1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 67264550HCID 67264550, compound

Product 1

HCID 87330275HCID 87330275, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

4-Nitro-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene (200 mg, 0.97 mmol), propargyl chloride (0.085 mL, 1.2 mmol), potassium carbonate (276 mg, 2.0 mmol) and THF (5 mL) were stirred together at 70° C. for 18 h. The reaction was then diluted with saturated aqueous NaHCO3 (10 mL), extracted with CH2Cl2 (2×10 mL), dried over MgSO4, filtered, and concentrated. The remaining residue was purified with silica gel chromatography (0-100% EtOAc in hexanes) to give 4-Nitro-10-prop-2-ynyl-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene as a brown oil (120 mg, 51%). MS (m/e) 245 (M+1).

Workup

  1. extractionextracted with CH2Cl2 (2×10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe remaining residue was purified with silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-84d750aad88d490398ff5726e1edbce2
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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