Sodium sulfate decahydrate → 3-(5-Methyl-2-phenyl-4-thiazolylmethoxy)-5-isoxazolylmethanol

HRID 1294187Notes

Reaction equation

HRID 1294187 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([C:20](OC)=[O:21])[O:17][N:16]=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][OH:21])[O:17][N:16]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 17861290Methyl 3-(5-methyl-2-phenyl-4-thiazolylmethoxy)-5-isoxazolecarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 178613523-(5-Methyl-2-phenyl-4-thiazolylmethoxy)-5-isoxazolylmethanolYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-(5-methyl-2-phenyl-4-thiazolylmethoxy)-5-isoxazolecarboxylate (5.27 g) in tetrahydrofuran (100 ml) was slowly added diisobutylaluminum hydride (0.95 M hexane solution, 60 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hr. Sodium sulfate 10 hydrate (17.01 g) was added to the reaction mixture and the mixture was further stirred at room temperature for 30 min. The insoluble materials were removed by filtration, and the filtrate was concentrated to give [3-(5-methyl-2-phenyl-4-thiazolylmethoxy)-5-isoxazolyl]methanol (3.88 g, 80%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 84-85° C.

Workup

  1. customat 0° C.
  2. stirringthe mixture was further stirred at room temperature for 30 min
  3. customThe insoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-34e5e3aea3614ad1a576d81527a06ca3
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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