Water → 5-[2-[2-Benzyloxy-4-[butyl(4-hydroxybutyl)amino]phenyl]vinyl]thiophene-2-carboaldehyde

HRID 85333Notes

Reaction equation

HRID 85333 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N:15]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:16][CH2:17][CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:12]=[CH:11][C:10]=1[CH:42]=[CH:43][C:44]1[S:48][C:47]([CH:49]=[O:50])=[CH:46][CH:45]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N:15]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:12]=[CH:11][C:10]=1[CH:42]=[CH:43][C:44]1[S:48][C:47]([CH:49]=[O:50])=[CH:46][CH:45]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 866676105-[2-[2-Benzyloxy-4-[butyl[4-(tert-butyldiphenylsiloxy) butyl]amino]phenyl]vinyl]thiophene-2-carboaldehyde

Product 1

HCID 866676115-[2-[2-Benzyloxy-4-[butyl(4-hydroxybutyl)amino]phenyl]vinyl]thiophene-2-carboaldehydeYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of tetrahydrofuran was dissolved 1.2 g (1.71 mmol) of 5-[2-[2-benzyloxy-4-[butyl[4-(tert-butyldiphenylsiloxy) butyl]amino]phenyl]vinyl]thiophene-2-carboaldehyde. To this mixture, 7.6 ml of tetrabutylammonium fluoride (1 mol/L solution in tetrahydrofuran) (7.6 mmol) was added dropwise with stirring at room temperature. The mixture was stirred for 1.5 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 residual liquid was purified by silica gel column chromatography to give 554 mg of a red crystal (yield: 70.1%).

Workup

  1. stirringThe mixture was stirred for 1.5 hours
  2. washwashing with a saturated saline solution
  3. dry with materialdrying over anhydrous sodium sulfate, and concentration
  4. customThe residual liquid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb9f5d2f77f943fab309d363ff061b56
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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