Water → (3-(4-Chlorophenyl)-5-methylisoxazol-4-yl)methanol

HRID 1911656Notes

Reaction equation

HRID 1911656 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:7]2[C:6]([CH2:4][OH:3])=[C:10]([CH3:11])[O:9][N:8]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66643827Ethyl 3-(4-chlorophenyl)-5-methylisoxazole-4-carboxylate

Product 1

HCID 15121509(3-(4-Chlorophenyl)-5-methylisoxazol-4-yl)methanolYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (373 mg, 1.4 mmol) in THF (17.9 mL) was added portionwise lithiumaluminiumhydride (29.6 mg, 0.78 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 3 h. The mixture was then cooled to 0° C. and water (29.0 μL) added followed by sodium hydroxide (15% solution, 29.0 μL) and then again water (84.0 μL) and the mixture then stirred overnight at room temperature. The precipitate was then filtered off and washed with THF. The combined washings and filtrate were then evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (204 mg, 65%) which was obtained as a white solid. MS: m/e=224.1 [M+H]+.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. filtrationThe precipitate was then filtered off
  3. washwashed with THF
  4. customThe combined washings and filtrate were then evaporated
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1)

Sources & evidence

ORD record
ord-ba6b032181c844bbaa0e8064ba03478c
Source dataset
uspto-grants-2013_12
Patent number
US08604062B2

Reaction notes

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