Water → HCID 86667563, compound

HRID 85271Notes

Reaction equation

HRID 85271 reaction equation
[CH2:1]([N:5]([CH2:39][CH2:40][CH2:41][CH3:42])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[S:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=2)=[C:8]([O:21][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=1)[CH2:2][CH2:3][CH3:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>O1CCCC1>[CH2:39]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[S:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=2)=[C:8]([OH:21])[CH:7]=1)[CH2:40][CH2:41][CH3:42]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86667556HCID 86667556, compound

Product 1

HCID 86667563HCID 86667563, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of tetrahydrofuran was dissolved 488 mg (0.82 mmol) of 5-[2-[4-dibutylamino-2-(tert-butyldiphenylsiloxy)phenyl]vinyl]thiophene-2-carboaldehyde, and 2.5 ml of tetrabutylammonium fluoride (1 mol solution in tetrahydrofuran) was added dropwise thereto with stirring at room temperature. The mixture was stirred for 35 minutes. After the reaction mixture was poured into water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 274 mg of a blackish brown crystal (yield: 93.6%).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for 35 minutes
  3. washwashing with a saturated saline solution
  4. dry with materialdrying over anhydrous sodium sulfate, and concentration
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f43ae6d82d244984a4b166d59ac8fcc3
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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