Water → Benzene, 1-ethynyl-3-nitro-

HRID 1159871Notes

Reaction equation

HRID 1159871 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]#[C:11][Si](C)(C)C)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C(OCC)C>[C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)#[CH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 114700401-Nitro-3-[2-(trimethylsilyl)ethynyl]-benzene

Product 1

HCID 76432Benzene, 1-ethynyl-3-nitro-Yield 89.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(3-nitrophenyl)-2-trimethylsilylacetylene (43 g, 0.197 mol) in diethylether (800 mL) is cooled to 0° C. under argon atmosphere. To this solution is added, dropwise over 30 min, a solution of TBAF (1M in THF, 217 mL, 0.217 mol) maintaining temperature below 10° C. The reaction mixture is stirred for 30 min at 0° C. The reaction mixture is poured into water and extracted with diethyl ether (×2). The organic layers are combined, washed with brine, and dried (Na2SO4). The solvents are removed under reduced pressure. The residue is purified by silica-gel chromatography with Hexane/EtOAc=20/1 to give orange oil (26 g).

Workup

  1. additionTo this solution is added, dropwise over 30 min
  2. extractionextracted with diethyl ether (×2)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvents are removed under reduced pressure
  6. customThe residue is purified by silica-gel chromatography with Hexane/EtOAc=20/1

Sources & evidence

ORD record
ord-3b48758630e44d3f8d461396d8d30cca
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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