1-Butanol → 2-(4-Hexylphenyl)-5-[4-(3-trimethylsilylpropoxy)phenyl]-1,3-thiazole

HRID 1587267Notes

Reaction equation

HRID 1587267 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].C(O)CCC.C1(C)C=CC(S(O[CH2:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])(=O)=O)=CC=1>O>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:19]=[CH:20][C:21]([O:24][CH2:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])=[CH:22][CH:23]=3)=[CH:16][N:17]=2)=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 14797Potassium HydroxideHCID 19757554HCID 19757554, compoundHCID 233547624-{2-(4-Hexylphenyl)thiazole-5-yl}phenol

Product 1

HCID 197575732-(4-Hexylphenyl)-5-[4-(3-trimethylsilylpropoxy)phenyl]-1,3-thiazoleYield 70.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

0.34 g (1.0 mM) of 2-(4-hexylphenyl)-5-(4-hydroxyphenyl)-1,3-thiazole, 0.07 g of 85%-KOH and 12 ml of n-butanol were mixed. To the mixture, 0.29 g (1.0 mM) of 3-(trimethylsilyl)propyl p-toluenesulfonate was added dropwise under stirring at 100° C., followed by further stirring for 9 hours at 100° C. After the reaction, the reaction mixture was poured into water and extracted with ethyl acetate, followed by washing with water and drying with anhydrous magnesium sulfate. The magnesium sulfate in the resultant mixture was filtered off and the filtrate was condensed into a solid, followed by purification by silica gel column chromatography (eluent: toluene) and recrystallization from a mixture solvent (ethanol/ethyl acetate) to obtain 0.32 g of 2-(4-hexylphenyl)-5-[4-(3-trimethylsilylpropoxy)phenyl]-1,3-thiazole (Yield: 70.8%). ##STR81##

Workup

  1. stirringby further stirring for 9 hours at 100° C
  2. customAfter the reaction
  3. extractionextracted with ethyl acetate
  4. washby washing with water
  5. dry with materialdrying with anhydrous magnesium sulfate
  6. filtrationThe magnesium sulfate in the resultant mixture was filtered off
  7. customcondensed into a solid
  8. customfollowed by purification by silica gel column chromatography (eluent: toluene) and recrystallization from a mixture solvent (ethanol/ethyl acetate)

Sources & evidence

ORD record
ord-3d4044e875fc41a684e5547f6f926eff
Source dataset
uspto-grants-1993_06
Patent number
US05217645

Reaction notes

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