Tetrahydrofuran → HCID 67813222, compound

HRID 2401354Notes

Reaction equation

HRID 2401354 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:15]([CH:20]=[O:21])=[N:16][O:17][C:18]=2[CH3:19])=[O:7])=[CH:4][CH:3]=1.[CH2:24]1COCC1.C[Mg]Cl.[Cl-].[NH4+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:15]([CH:20]([OH:21])[CH3:24])=[N:16][O:17][C:18]=2[CH3:19])=[O:7])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86666718HCID 86666718, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 67813222HCID 67813222, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a resealable vial was added 4-(2-(4-chlorobenzoyl)phenyl)-5-methylisoxazole-3-carbaldehyde from Example 15 (0.100 g, 0.307 mmol) and THF (2.0 mL). The vial was sealed and cooled to −78° C. before addition of methylmagnesium chloride (0.107 mL, 0.322 mmol). The reaction was stirred at −78° C. for 30 min before addition of ammonium chloride solution and water. The aqueous was extracted with EtOAc and the combined layers washed with brine, dried over Na2SO4, filtered, and concentrated to afford crude (4-chlorophenyl)(2-(3-(1-hydroxyethyl)-5-methylisoxazol-4-yl)phenyl)methanone (0.092 g, 0.269 mmol).

Workup

  1. customThe vial was sealed
  2. extractionThe aqueous was extracted with EtOAc
  3. washthe combined layers washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e0c822f7c1c744e0a75bd1d1f0411938
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

Loading…