Chloroform → HCID 178467845, compound

HRID 1658897Notes

Reaction equation

HRID 1658897 reaction equation
[N+]([CH:4]([CH3:14])[CH2:5][CH2:6][C:7]([C-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)=[O:8])([O-])=O.[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20].C(Cl)(Cl)Cl.C(=O)(O)[O-:26].[Na+]>C(COC)OC.O.[Cl-].[Cl-].[Cl-].[Ti+3].[O-2].[O-2].[Ti+4]>[O:26]=[C:4]([CH3:14])[CH2:5][CH2:6][C:7]([C-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)=[O:8].[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20]

Participants

8

Reactant 3

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 178446908HCID 178446908, compound

Product 1

HCID 178467845HCID 178467845, compound

Reagents, catalysts & solvents 4

HCID 162651Titanium oxide (Ti3O)CatalystHCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

The nitro compound (315 mg; 1 m mole) in glyme (5 ml) was treated with titanium trichloride (4 m mole) in water (5 ml) under N2 with stirring at room temperature. After 2 days a further 4 m mole of TiCl3 was added and stirring was continued for 24 hrs. The product was poured into chloroform (50 ml) and saturated sodium bicarbonate was added until precipitation of titanium dioxide was complete. The two layers were filtered through `Hiflo` and the chloroform layer was washed with sodium bicarbonate solution, water and dried (sodium sulphate) to yield an oil which was chromatographed on silica to yield starting material (eluted with 5% ethyl acetate/toluene) and 4-oxopentanoyl ferrocene (30 mg; 10.6%) NMR 8, 4.75 (t, 2H); 4.44 (t, 2H); 4.21 (S, 5H); 3.1 2.6 (A2B2, 4H); 2.21 (S, 3H).

Workup

  1. stirringstirring
  2. filtrationThe two layers were filtered through `Hiflo` and the chloroform layer
  3. washwas washed with sodium bicarbonate solution, water
  4. dry with materialdried (sodium sulphate)
  5. customto yield an oil which
  6. customwas chromatographed on silica
  7. customto yield
  8. washmaterial (eluted with 5% ethyl acetate/toluene) and 4-oxopentanoyl ferrocene (30 mg; 10.6%) NMR 8, 4.75 (t, 2H); 4.44 (t, 2H); 4.21 (S, 5H); 3.1 2.6 (A2B2, 4H); 2.21 (S, 3H)

Sources & evidence

ORD record
ord-1cda9e755b66407cb0d124a2a3ce45f3
Source dataset
uspto-grants-1976_06
Patent number
US03966783

Reaction notes

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