Tetrabutylammonium Fluoride → HCID 58670153, compound

HRID 1353173Notes

Reaction equation

HRID 1353173 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]([O:14][Si](C(C)(C)C)(C)C)[CH2:11][CH:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[CH2:1]([N:8]1[CH2:13][CH:12]([OH:14])[CH2:11][CH:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[C:9]1=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69428146HCID 69428146, compound

Product 1

HCID 58670153HCID 58670153, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of compound 1E (2.33 g, 5.36 mmol) in 13 mL of THF at room temperature under argon was added (in one portion) 6.7 mL or 1M tetrabuylammonium fluoride (in THF, 6.7 mmol). After 1 h, the reaction mixture was diluted with EtOAc and washed once with saturated sodium bicarbonate solution. The organic extract was dried over MgSO4, filtered and evaporated under reduced pressure. The resulting white solid was dried in vacuo to give the title compound (1.74 g, 100% material balance) and used in the next reaction without additional purification. MS [M+H]+: found 321.

Workup

  1. washwashed once with saturated sodium bicarbonate solution
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting white solid was dried in vacuo

Sources & evidence

ORD record
ord-611ed57f16ed4b86a388b22368531082
Source dataset
uspto-grants-2007_05
Patent number
US07220859B2

Reaction notes

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