Water → 3-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine

HRID 1895950Notes

Reaction equation

HRID 1895950 reaction equation
C[Si](C)(C)C(=[C:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]1C=CN=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])C#CC.O.[F-].[CH2:26]([N+:30](CCCC)(CCCC)CCCC)[CH2:27]CC.O.[CH2:44]1[CH2:48]OC[CH2:45]1>>[N+:19]([C:14]1[C:13]([N:8]2[CH2:7][CH2:12][C:11](=[CH:48][C:44]#[CH:45])[CH2:10][CH2:9]2)=[N:30][CH:26]=[CH:27][CH:15]=1)([O-:21])=[O:20]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 1317308274-(1-Trimethysilylbut-2-ynylidenepiperidin-1-yl)-3-nitropyridine

Product 1

HCID 866273353-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine

Procedure

A solution of Compound 1b (0.57 g, 1.81 mmol), tetra-n-butylammonium fluoride hydrate (0.57 g, 2.03 mmol) in 38 mL of THF was stirred at r.t. for 2 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether 1:9) giving the title product (0.21 g).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. customdried on Na2SO4
  4. customevaporated to dryness in vacuo
  5. customto afford a residue, which
  6. customwas purified by flash chromatography (EtOAc—Petroleum Ether 1:9)

Sources & evidence

ORD record
ord-456ac313f1f14e76b8d5e4759a0bfedb
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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