Tetrabutylammonium Fluoride → HCID 59457702, compound

HRID 1711100Notes

Reaction equation

HRID 1711100 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]#[C:15][Si](C)(C)C)[S:13][C:6]=12.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(O)=O>[C:14]([C:12]1[S:13][C:6]2[C:7](=[N:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]2[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:2]=2[F:1])[CH:11]=1)#[CH:15]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59457700HCID 59457700, compound

Product 1

HCID 59457702HCID 59457702, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the alkyne 409 (2.2 g, 5.69 mmol) in THF (30 ml) was added a solution of TBAF (8.53 mL, 1.5 eq, 1M soln in THF) in HOAc (30 ml), and the reaction mixture was stirred at RT overnight. It was then concentrated to dryness and partitioned between water and EtOAc. The organic phase was washed well with satd. NaHCO3 soln, collected, dried over anhydrous Na2SO4, filtered and concentrated. The crude mixture was adsorbed onto silica gel then purified by column chromatography (30% EtOAc in hexane) to afford 410 (1.4 g, 72% yield). LCMS: 415.2 (M+H).

Workup

  1. concentrationIt was then concentrated to dryness
  2. custompartitioned between water and EtOAc
  3. washThe organic phase was washed well with satd
  4. customNaHCO3 soln, collected
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthen purified by column chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-8f544143979d4417ac4f620b98895726
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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