Methanol → HCID 67811908, compound

HRID 2401357Notes

Reaction equation

HRID 2401357 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>[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

6

Reactant 4

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

Product 1

HCID 67811908HCID 67811908, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a round bottomed flask was added (4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)methyl benzoate from Example 12 (0.780 g, 1.806 mmol), THF (4 mL), MeOH (4 mL), and water (2 mL). The solution was cooled to 0° C. before addition of lithium hydroxide monohydrate (0.227 g, 5.42 mmol). The reaction was stirred at 0° C. for 45 min before diluting with water and extracting with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (4-chlorophenyl)(2-(5-(hydroxymethyl)-3-methylisoxazol-4-yl)phenyl)methanone (0.451 g, 1.376 mmol). LC/MS m/z 328 [M+H]+.

Workup

  1. extractionextracting with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-45e815b87fd54b0c867442fa64820bff
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

Loading…