2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → (NE,S)-N-[2-[tert-butyl(dimethyl)silyl]oxyethylidene]-2-methylpropane-2-sulfinamide

HRID 627280Notes

Reaction equation

HRID 627280 reaction equation
[Si:1]([O:8][CH2:9][CH:10]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:12][C:13]([S@@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[Si:1]([O:8][CH2:9]/[CH:10]=[N:18]/[S@:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 16007023(NE,S)-N-[2-[tert-butyl(dimethyl)silyl]oxyethylidene]-2-methylpropane-2-sulfinamideYield 61.7%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-((tert-butyldimethylsilyl)oxy)acetaldehyde (Aldrich, 15 g, 86.05 mmol) in DCM (200 mL) at room temperature was added copper(II) sulfate (41.2 g, 258.16 mmol) and (S)-2-methylpropane-2-sulfinamide (Aldrich, 15.64 g, 129.08 mmol). The reaction mixture was stirred overnight at room temperature, then filtered through celite, washed with DCM and concentrated to afford an oil. Silica gel chromatography (0%-25% ethyl acetate/hexanes) afforded the title compound (14.73 g, 61.7%) as a colorless oil.

Workup

  1. filtrationfiltered through celite
  2. washwashed with DCM
  3. concentrationconcentrated
  4. customto afford an oil

Sources & evidence

ORD record
ord-dbb08ed2d4554e48963ae006dee0bb71
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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