[1-(3-Chlorophenyl)-2-nitroethoxy]triethylsilane → HCID 22021029, compound

HRID 1767000Notes

Reaction equation

HRID 1767000 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:13][Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[CH2:9][N+:10]([O-])=O)[CH:5]=[CH:6][CH:7]=1>[Ni].CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:13][Si:14]([CH2:15][CH3:16])([CH2:19][CH3:20])[CH2:17][CH3:18])[CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22021350[1-(3-Chlorophenyl)-2-nitroethoxy]triethylsilane

Product 1

HCID 22021029HCID 22021029, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel (1 g) was washed with distilled water five times and methanol three times. [1-(3-Chloro-phenyl)-2-nitro-ethoxy]-triethyl-silane (10 g, 0.032 mol) and Raney nickel in methanol (100 mL) was hydrogenated (35 psi) at room temperature for 14 h. The reaction mixture was filtered through a pad of celite and rinsed with methanol. Concentration of the filtrate to dryness gave the title compound (5.6 g, 62%) as a colorless oil which was used for the next step without purification. 1H NMR (300 MHz, CDCl3) δ 7.32 (1H, s), 7.18-7.26 (3H, m), 4.70 (1H, t, J=5.8 Hz), 2.86 (2H, m), 0.89 (9H, t, J=7.9 Hz), 0.56 (6H, q, J=7.8 Hz). LRMS (M+H)+ m/z 286.

Workup

  1. washRaney nickel (1 g) was washed with distilled water five times and methanol three times
  2. customat room temperature
  3. customfor 14 h
  4. filtrationThe reaction mixture was filtered through a pad of celite
  5. washrinsed with methanol

Sources & evidence

ORD record
ord-3b3497f7626f48deb374ed11f6fffc8a
Source dataset
uspto-grants-2007_06
Patent number
US07232826B2

Reaction notes

Loading…