Tetrabutylammonium Fluoride → HCID 68838760, compound

HRID 660514Notes

Reaction equation

HRID 660514 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[CH:11][C:10]=1[N:24]1[S:28](=[O:30])(=[O:29])[N:27](CC[Si](C)(C)C)[C:26](=[O:37])[CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[CH:11][C:10]=1[N:24]1[S:28](=[O:30])(=[O:29])[NH:27][C:26](=[O:37])[CH2:25]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68843385HCID 68843385, compound

Product 1

HCID 68838760HCID 68838760, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(2-benzyloxy-4-phenethyloxyphenyl)-1 , 1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (47 mg, 0.087 mmol) and tetrabutylammonium fluoride (0.5M in THF, 0.35 mL, 0.175 mmol) in THF (5 mL) is refluxed for 1 h. The mixture is cooled to RT, concentrated, and extracted with EtOAc. The organic phase is washed with 1N HCl and is dried over magnesium sulfate. The solvent is removed under reduced pressure to afford the title compound: (M−1)−=437.

Workup

  1. concentrationconcentrated
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with 1N HCl
  4. dry with materialis dried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-b3a90fe885e24fde88764229513757c5
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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