Water → [4-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]-2,5-dimethylphenyl]methanol

HRID 85255Notes

Reaction equation

HRID 85255 reaction equation
[CH2:1]([N:5]([CH2:43][CH2:44][CH2:45][CH3:46])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][O:22][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:16][C:15]=2[CH3:40])=[C:8]([O:41][CH3:42])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>O1CCCC1>[CH2:43]([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[C:15]([CH3:40])=[CH:16][C:17]([CH2:21][OH:22])=[C:18]([CH3:20])[CH:19]=2)=[C:8]([O:41][CH3:42])[CH:7]=1)[CH2:44][CH2:45][CH3:46]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 68008984Dibutyl[4-[2-[4-(tert-butyldiphenylsiloxymethyl)-2,5-dimethylphenyl]vinyl]-3-methoxyphenyl]amine

Product 1

HCID 68009049[4-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]-2,5-dimethylphenyl]methanolYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran was dissolved 2.7 g (4.26 mmol) of dibutyl[4-[2-[4-(tert-butyldiphenylsiloxymethyl)-2,5-dimethylphenyl]vinyl]-3-methoxyphenyl]amine, and 13.0 ml of tetrabutylammonium fluoride (1 mol solution in tetrahydrofuran) was added dropwise thereto with stirring at room temperature. The mixture was stirred for 3 hours. 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 1.57 g of a yellow liquid (yield: 93.5%).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for 3 hours
  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-3ca5ffc00aef45e0a0aba300c5cf45df
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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