Sulfuric acid magnesium salt (1:1) → HCID 117776858, compound

HRID 709421Notes

Reaction equation

HRID 709421 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH3:28][C:29]([S@:32]([NH2:34])=[O:33])([CH3:31])[CH3:30].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)/[CH:5]=[N:34]/[S@@:32]([C:29]([CH3:31])([CH3:30])[CH3:28])=[O:33]

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5881603,5-DifluorobenzaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 117776858HCID 117776858, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-difluorobenzaldehyde (1.00 g, 7.04 mmol, 1.00 equiv) in CH2Cl2 (20 mL) were added pyridinium p-toluenesulfonate (0.089 g, 0.35 mmol, 0.05 equiv), (R)-(+)-2-methylpropane-2-sulfinamide (0.852 g, 7.03 mmol, 1.00 equiv), and MgSO4 (4.2 g, 35.00 mmol, 5.00 equiv). The resulting mixture was stirred overnight at room temperature. The reaction mixture was filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (silica gel, 20% EtOAc in petroleum ether) to provide 500 mg (29%) of the title compound as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by flash chromatography (silica gel, 20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-b7c1c717e819492ba830ecc3e7b47d1d
Source dataset
uspto-grants-2015_11
Patent number
US09181200B2

Reaction notes

Loading…