Methyl 3-formylbenzoate → methyl 3-[(E)-[(R)-tert-butylsulfinyl]iminomethyl]benzoate

HRID 64448Notes

Reaction equation

HRID 64448 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[CH3:13][C:14]([S@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>ClCCl.S([O-])([O-])(=O)=O.[Cu+2]>[C:14]([S@:17](/[N:19]=[CH:1]/[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:18])([CH3:16])([CH3:15])[CH3:13]

Participants

5

Reactant 2

HCID 639145Methyl 3-formylbenzoateHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 90072426methyl 3-[(E)-[(R)-tert-butylsulfinyl]iminomethyl]benzoateYield 14.3%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 3.0 g of methyl 3-formylbenzoate, 2.25 g of (R)-2-methyl-2-propanesulfinamide, and 6.0 g of copper (II) sulfate in 50 ml of dichloromethane was stirred overnight. The reaction mixture was filtered over Celite and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 700 mg of methyl 3-[(E)-{[(R)-tert-butylsulfinyl]imino}methyl]benzoate.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. customthe solvent was then evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1279496b53e34c868d6b3cccc4f50013
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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