Tetrahydrofuran → 5-Ethynylnicotinonitrile

HRID 606784Notes

Reaction equation

HRID 606784 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C[Si]([C:28]#[C:29][C:30]1[CH:31]=[N:32][CH:33]=[C:34]([CH:37]=1)[C:35]#[N:36])(C)C>C(N(CC)CC)C.C(OCC)(=O)C>[C:29]([C:30]1[CH:31]=[N:32][CH:33]=[C:34]([CH:37]=1)[C:35]#[N:36])#[CH:28]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 161156995-[2-(Trimethylsilyl)ethynyl]pyridine-3-carbonitrile

Product 1

HCID 224165635-EthynylnicotinonitrileYield 74.1%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (50.0 mL, 50.0 mmol) to a suspension of 5-trimethylsilanylethynyl-nicotinonitrile (10.0 g, 50.0 mmol), (prepared as described in PREPARATION 3), in triethylamine (98 mL) at 0° C. After 5 min, dilute the reaction mixture with ethyl acetate and wash twice with water. Back-extract the combined aqueous washes twice with ethyl acetate. Wash the combined organic layers with a saturated aqueous solution of sodium chloride, dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with a gradient from 98:2 to 90:10 dichloromethane:ethyl acetate, to give the title compound as a white crystalline solid (4.75 g, 74%).

Workup

  1. washwash twice with water
  2. extractionBack-extract the combined aqueous washes twice with ethyl acetate
  3. washWash the combined organic layers with a saturated aqueous solution of sodium chloride
  4. dry with materialdry (sodium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue by silica gel chromatography
  8. washeluting with a gradient from 98:2 to 90:10 dichloromethane

Sources & evidence

ORD record
ord-5ab99e3f274c495a9ed35ee2c13b5a67
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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