2-Propanone, 1-nitro- → HCID 12708179, compound

HRID 1833605Notes

Reaction equation

HRID 1833605 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11]S)=[CH:2]1.[N+](C([N+]([O-])=O)=O)([O-])=O.[N+:21]([CH2:24][C:25](=[O:27])[CH3:26])([O-:23])=[O:22]>C1C=CC=CC=1.B(F)(F)F.CCOCC.FC(F)(F)C(O)=O>[CH3:26][C:25]1([CH2:24][N+:21]([O-:23])=[O:22])[C:2]2[NH:1][C:9]3[C:4]([C:3]=2[CH2:10][CH2:11][O:27]1)=[CH:5][CH:6]=[CH:7][CH:8]=3

Participants

7

Reactant 3

HCID 662962-Propanone, 1-nitro-HCID 122442792-(1H-indol-3-yl)ethane-1-thiolHCID 54223030Nitro ketone

Product 1

HCID 12708179HCID 12708179, compound

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidCatalystHCID 8000Boron trifluoride etherateCatalystHCID 241BenzeneSolvent2×

Procedure

To a solution of 322 mg of tryptophol (II, R2, R3, R4, R5, R6 = H and X1 =OH) and 248 mg of the nitroketone, nitro-2-propanone, in 100 ml of benzene is added five drops of boron trifluoride etherate and three drops of trifluoroacetic acid. The reaction mixture is stirred and heated at reflux under water-separator for 18 hr. The benzene solution is cooled, washed with 10% sodium bicarbonate solution, water, saturated brine solution, and dried over magnesium sulfate. The solvent is removed and the residue is subjected to chromatography on silica gel. Elution with chloroform gives the title compound, νmaxCHCl3 3450, 1550cm-1, nmr (CHCl3) δ1.68 (s, 3H), 2.84 (t, 2H), 4.10 (t, 2H).

Workup

  1. temperatureheated
  2. temperatureat reflux under water-separator for 18 hr
  3. washwashed with 10% sodium bicarbonate solution, water, saturated brine solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed
  6. washElution with chloroform

Sources & evidence

ORD record
ord-4154e6db5f284edaba0cc6835f2a70fa
Source dataset
uspto-grants-1978_01
Patent number
US04066779

Reaction notes

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