Dimethyl Sulfoxide → HCID 67814253, compound

HRID 2401343Notes

Reaction equation

HRID 2401343 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[C:27]([CH2:32][O:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)=[N:28][O:29][C:30]=2[CH3:31])[OH:19])=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[C:27]([CH2:32][O:33][CH2:34][C:35]3[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=3)=[N:28][O:29][C:30]=2[CH3:31])=[O:19])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67814280HCID 67814280, compound

Product 1

HCID 67814253HCID 67814253, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a round bottomed flask was added DCM (4 mL) and oxalyl chloride (28.0 μl, 0.320 mmol) before the solution was cooled to −78° C. To this solution was added DMSO (37.9 μl, 0.533 mmol) and the reaction stirred at −78° C. for 15 min before addition of (4-chlorophenyl)(2-(3-((4-methoxybenzyloxy)methyl)-5-methylisoxazol-4-yl)phenyl)methanol (120 mg, 0.267 mmol) dissolved in DCM. The solution was stirred for an additional 15 min before addition of Et3N (112 μl, 0.800 mmol) and the reaction warmed to room temperature. Water was added and the layers separated. The aqueous was extracted with DCM and the combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (4-chlorophenyl)(2-(3-((4-methoxybenzyloxy)methyl)-5-methylisoxazol-4-yl)phenyl)methanone. LC/MS m/z 448 [M+H]+.

Workup

  1. temperaturethe reaction warmed to room temperature
  2. customthe layers separated
  3. extractionThe aqueous was extracted with DCM
  4. dry with materialthe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-7b5c164a023c49ceb056fab6c38539d0
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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