Ammonium Chloride → HCID 68709854, compound

HRID 1441710Notes

Reaction equation

HRID 1441710 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([CH2:20][CH2:21][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])=[O:23])[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4].[Cl-].[NH4+]>C1COCC1.CO>[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([CH2:20][CH2:21][CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[OH:23])[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 68708924HCID 68708924, compound

Product 1

HCID 68709854HCID 68709854, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (20 mg, 0.53 mmol) was added to a mixed solution of 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]-1-(2-methoxyphenyl)-1-propanone (458 mg, 1.11 mmol) in THF (10 ml) and methanol (10 ml) at room temperature, and the resulting mixture was stirred at the same temperature for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/1). The solvent was distilled off under reduced pressure, and the residue was recrystallized from a diethyl ether/n-hexane mixed solvent, to thereby obtain 336 mg (yield: 73%) of 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]-1-(2-methoxyphenyl)-1-propanol as a white powder.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/1)
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was recrystallized from a diethyl ether/n-hexane mixed solvent

Sources & evidence

ORD record
ord-35ee631580ab49319fa827c86b3cd41a
Source dataset
uspto-grants-2010_02
Patent number
US07655680B2

Reaction notes

Loading…