Tetrabutylammonium Fluoride → HCID 67571000, compound

HRID 582166Notes

Reaction equation

HRID 582166 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]1[N:9]=[CH:8][N:7]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1.[F-:29].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[F:29][CH2:2]/[CH:3]=[CH:4]/[C:5]1[N:9]=[CH:8][N:7]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67571165HCID 67571165, compound

Product 1

HCID 67571000HCID 67571000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of E-1-bromo-3(1-trityl-1,2,4-triazol-3-yl)prop-2-ene) (34.47 g, prepared as described in Example 12) in dry dichloromethane (150 ml) was treated, under nitrogen, with tetrabutylammonium fluoride (160 ml, 1M in tetrahydrofuran). The mixture was heated under reflux for thirty minutes, cooled, washed with water (3×100 ml), dried over magnesium sulphate and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ether (25:2) as eluant, to give E-1-fluoro-3(1-trityl-1,2,4-triazol-3-yl)prop-2-ene (19.37 g, m.p. 149° C). NMR (CDCl3): δ 4.95, 5.15(2H,dd), 6.7-6.9(2H,m), 7.1-7.3(15H,m), 7.9(1H,s). JCH=CH 16.1 Hz, JHF 46.8 Hz. 19F NMR (CDCl3): -216.4 ppm vs. CFCl3.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for thirty minutes
  3. temperaturecooled
  4. washwashed with water (3×100 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-2fc649e682de4719b4680ecf8bf70705
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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