HCID 13015380, compound → HCID 13015381, compound

HRID 1863355Notes

Reaction equation

HRID 1863355 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:22][C:23](OC)=[O:24])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([CH2:22][CH2:23][OH:24])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 13015380HCID 13015380, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13015381HCID 13015381, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4,5-bis(p-methoxyphenyl)-2-thiazoleacetic acid, methyl ester (2.5 g.; 0.0068 mole) and THF (10 ml.) was added dropwise by syringe to an ice cooled slurry of lithium aluminum hydride (0.55 g.; 0.0145 mole) and THF (20 ml.). Stirring was continued for an additional 1.25 hours at ambient temperature. The reaction was quenched by the dropwise addition of water (2 ml. via syringe) and then concentrated by rotary evaporation. The residue was slurried with water, taken to pH 4 with 6 N sulfuric acid, and extracted with methylene chloride. The extracts were washed with water, dried (sodium sulfate), and concentrated by rotary evaporation. The crude mixture was chromatographed (HPLC) with 50% ethyl acetate in benzene through silica gel and then recrystallized from ether-pentane to afford 0.82 g. (35% yield) 4,5-bis(4-methoxyphenyl)-2-thiazole ethanol; m.p. 101°-104° C.

Workup

  1. customThe reaction was quenched by the dropwise addition of water (2 ml. via syringe)
  2. concentrationconcentrated by rotary evaporation
  3. extractionextracted with methylene chloride
  4. washThe extracts were washed with water
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated by rotary evaporation
  7. customThe crude mixture was chromatographed (HPLC) with 50% ethyl acetate in benzene through silica gel
  8. customrecrystallized from ether-pentane
  9. customto afford 0.82 g

Sources & evidence

ORD record
ord-e301d93df46843e3af088a9106388e23
Source dataset
uspto-grants-1979_09
Patent number
US04168315

Reaction notes

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