3-(Trifluoromethoxy)benzaldehyde → HCID 89421013, compound

HRID 246275Notes

Reaction equation

HRID 246275 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O.[CH3:14][C:15]([S@@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>ClCCl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6](/[CH:7]=[N:20]/[S@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 6051393-(Trifluoromethoxy)benzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89421013HCID 89421013, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 50 ml round-bottomed flask, 3-(trifluoromethoxy)benzaldehyde (400 mg, 2.1 mmol) was dissolved in dichloromethane (12 ml) and (S)-2-methylpropane-2-sulfinamide (281 mg, 2.31 mmol) and anhydrous copper (II) sulfate (739 mg, 4.63 mmol) were added. The reaction mixture was stirred at room temperature overnight then filtered through a glass microfiber filter, rinsing with dichloromethane. The filtrate was concentrated and the residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-20% EtOAc) to afford 430 mg (70%) of (S)-2-methyl-propane-2-sulfinic acid 1-(3-trifluoromethoxy-phenyl)-meth-(E)-ylideneamide as a light yellow oil.

Workup

  1. filtrationthen filtered through a glass microfiber
  2. filtrationfilter
  3. washrinsing with dichloromethane
  4. concentrationThe filtrate was concentrated
  5. customthe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-20% EtOAc)

Sources & evidence

ORD record
ord-add68201d0a94cd284ed5e6de2bf8b44
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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