Dimethyl Sulfoxide → HCID 86666718, compound

HRID 2401353Notes

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][OH:33])=[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:13]=[CH:14][C:15]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[C:27]([CH:32]=[O:33])=[N:28][O:29][C:30]=2[CH3:31])=[O:19])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a round bottomed flask was added CH2Cl2 and oxalyl chloride (1.21 mL, 13.8 mmol) before the solution was cooled to −78° C. To this solution was added DMSO (1.47 mL, 20.65 mmol) and the solution stirred for 15 min before addition of (4-chlorophenyl)(2-(3-(hydroxymethyl)-5-methylisoxazol-4-yl)phenyl)methanol (1.14 g, 3.44 mmol) dissolved in CH2Cl2. The reaction was stirred for 15 min at −78° C. before addition of Et3N (3.84 mL, 27.5 mmol) and warming the reaction to room temperature overnight. This reaction was diluted with water and the layers separated. The aqueous was extracted with CH2Cl2 and the combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford 4-(2-(4-chlorobenzoyl)phenyl)-5-methylisoxazole-3-carbaldehyde (1.10 g, 3.38 mmol). LC/MS m/z 326 [M+H]+.

Workup

temperaturewarming
customthe reaction to room temperature overnight
customthe layers separated
extractionThe aqueous was extracted with CH2Cl2
dry with materialthe combined organics were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record: ord-741d9cb7a5ea41038fc323af77a7940b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796261B2

Reaction notes

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