Ammonium Chloride → 3-[2-(4,5-Diphenyl-2-thiazolyl)ethyl]phenol

HRID 1461757Notes

Reaction equation

HRID 1461757 reaction equation
C([Li])CCC.[CH3:6][C:7]1[S:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1.Br[CH2:25][C:26]1[CH:27]=[C:28]([CH:37]=[CH:38][CH:39]=1)[O:29][Si](C)(C)C(C)(C)C.[Cl-].[NH4+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCCCCC.C1COCC1.Cl.C(OCC)C>[C:12]1([C:10]2[N:11]=[C:7]([CH2:6][CH2:25][C:26]3[CH:27]=[C:28]([OH:29])[CH:37]=[CH:38][CH:39]=3)[S:8][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

10

Reactant 5

HCID 25517Ammonium ChlorideHCID 773652-Methyl-4,5-diphenylthiazoleHCID 2724141Tetrabutylammonium FluorideHCID 10040514[3-(Bromomethyl)phenoxy](tert-butyl)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 150069043-[2-(4,5-Diphenyl-2-thiazolyl)ethyl]phenolYield 58%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent4×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.53 g, 24 mmol) in hexane (9.5 mL) was added dropwise to a stirred solution of 2-methyl-4,5-diphenylthiazole (5 g, 20 mmol) in dry THF (150mL,) maintained at -78° C. under an atmosphere of nitrogen. After 25 minutes a solution of [3-(bromomethyl)phenoxy]dimethyl(1,1-dimethylethyl)silane (6.60 g, 22mmol) in THF (10mL) was added dropwise, the mixture stirred at -78° C. for 10 minutes and the allowed to warm to room temperature. The reaction mixture was poured onto saturated ammonium chloride solution, extracted with CH2Cl2, the extracts combined, dried over sodium sulfate and concentrated in vacuo to leave an oil which was dissolved in THF (25 mL). A solution of tetra-n-butylammonium fluoride (6.77 g, 26 mmol) in THF (25.86 mL) was added and the mixture stirred at room temperature for 30 minutes before being diluted with 1N HCl solution (100 mL). The mixture was extracted with CH2Cl2, the combined extracts dried over sodium sulfate and concentrated to leave an oil. Chromatography on a column of silica gel using a mixture of hexanes and diethyl ether (2:1) as eluent furnished 3-[2-(4,5-diphenyl-2-thiazolyl)ethyl]phenol (4.13 g, 58%), mp 166°-168° C. after recrystallization from a mixture of hexanes and CH2Cl2.

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto leave an oil which
  6. stirringthe mixture stirred at room temperature for 30 minutes
  7. extractionThe mixture was extracted with CH2Cl2
  8. dry with materialthe combined extracts dried over sodium sulfate
  9. concentrationconcentrated
  10. customto leave an oil

Sources & evidence

ORD record
ord-7919114cf47c4a468378cc435560f90a
Source dataset
uspto-grants-1991_12
Patent number
US05077305

Reaction notes

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