Tetrabutylammonium Fluoride → HCID 22350098, compound

HRID 896680Notes

Reaction equation

HRID 896680 reaction equation
C([Si](C)(C)[O:6][C:7]([C:34]1[CH:39]=[CH:38][C:37]([S:40][CH3:41])=[CH:36][CH:35]=1)([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[CH:18]=[C:19]([C:27]([S:30]([CH3:33])(=[O:32])=[O:31])([CH3:29])[CH3:28])[CH:20]=[C:21]3[C:26]=2[N:25]=[CH:24][CH:23]=[CH:22]3)[CH:12]=1)C#N)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.[OH-].[Na+].C(OCC)(=O)C>[CH3:33][S:30]([C:27]([C:19]1[CH:20]=[C:21]2[C:26](=[C:17]([C:13]3[CH:12]=[C:11]([CH2:10][C:7]([C:34]4[CH:35]=[CH:36][C:37]([S:40][CH3:41])=[CH:38][CH:39]=4)=[O:6])[CH:16]=[CH:15][CH:14]=3)[CH:18]=1)[N:25]=[CH:24][CH:23]=[CH:22]2)([CH3:28])[CH3:29])(=[O:31])=[O:32]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22350132HCID 22350132, compound

Product 1

HCID 22350098HCID 22350098, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of crude cyanohydrin from Step 2 above in THF (25 mL) was added tetrabutylammonium fluoride (1M, THF, 6.5 mL, 6.5 mmol) dropwise. The resulting reaction mixture was stirred at 21° C. for 30 min and diluted with a sodium hydroxide solution and ethyl acetate. The organic extracts were washed (1N NaOH 2×), (brine), dried (MgSO4), filtered and concentrated.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (1N NaOH 2×), (brine),
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ae24eda3a5e74628926c4d3c887f71fa
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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