Methanol → HCID 67811908, compound

HRID 2401336Notes

Reaction equation

HRID 2401336 reaction equation
C([O:9][CH2:10][C:11]1[O:15][N:14]=[C:13]([CH3:16])[C:12]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[O:31])[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)(=O)C1C=CC=CC=1.C1COCC1.CO.O.[OH-].[Li+]>O.CCOC(C)=O>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:12]2[C:13]([CH3:16])=[N:14][O:15][C:11]=2[CH2:10][OH:9])=[O:31])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67814343HCID 67814343, compound

Product 1

HCID 67811908HCID 67811908, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottomed flask was added (4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)methyl benzoate (32.7 mg, 0.076 mmol), THF (3 mL), MeOH (3 mL), and water (1.5 mL). This solution was cooled to 0° C. before addition of Lithium Hydroxide Monohydrate (9.53 mg, 0.227 mmol) and the reaction stirred at 0° C. for 1 h before diluting with water and EtOAc. The layers were separated and the aqueous extracted with EtOAc (3×). The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated to afford crude (4-chlorophenyl)(2-(5-(hydroxymethyl)-3-methylisoxazol-4-yl)phenyl)methanone.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous extracted with EtOAc (3×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5d778073ed7a49218e311e6b6d85d6ad
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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