2-(Trimethylsilyl)ethanol → HCID 19756384, compound

HRID 893621Notes

Reaction equation

HRID 893621 reaction equation
CC(C)([O-])C.[K+].[CH3:7][Si:8]([CH3:13])([CH3:12])[CH2:9][CH2:10][OH:11].Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1>CN(C=O)C>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([O:11][CH2:10][CH2:9][Si:8]([CH3:13])([CH3:12])[CH3:7])=[N:16][CH:17]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 180132-(Trimethylsilyl)ethanolHCID 783082-Chloro-5-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 19756384HCID 19756384, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium t-butoxide (25.8 g) was added portionwise over 20 minutes to a solution of 2-(trimethylsilyl)ethanol (20.8 g) and 2-chloro-5-nitropyridine (27.8 g) in DMF (170 ml). The mixture was stirred for 18 hours and then poured into ice-water (900 ml). The mixture was extracted with ethyl acetate (3×300 ml) and the extracts were washed with water (200 ml), followed by saturated sodium chloride solution (200 ml) and dried (MgSO4). Volatile material was removed by evaporation to give 5-nitro-2-[2-(trimethylsilyl)ethoxy]pyridine (34.9 g) as an oil; NMR: 0.05(s,9H), 1.1-1.2(m,2H), 4.45-4.55(m,2H), 6.75(d,1H), 8.3(dd,1H), 9.05(d,1H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×300 ml)
  2. washthe extracts were washed with water (200 ml)
  3. dry with materialdried (MgSO4)
  4. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-83d5a301a0a64cd8ac9b1022e6029934
Source dataset
uspto-grants-1992_06
Patent number
US05126344

Reaction notes

Loading…