Hydrochloric Acid → HCID 68887556, compound

HRID 1294197Notes

Reaction equation

HRID 1294197 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:20]=[C:19]([C:21](OC)=[O:22])[O:18][N:17]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:20]=[C:19]([CH2:21][OH:22])[O:18][N:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 17861329HCID 17861329, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 68887556HCID 68887556, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-isoxazolecarboxylate (9.2 g) and tetrahydrofuran (200 mL) was added lithium aluminum hydride (1.06 g) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Dilute hydrochloric acid was added to acidify the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (4.90 g, 58%) of [3-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-isoxazolyl]methanol from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 115-116° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0feb61db05744e41ba37e334373aa537
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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