2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → HCID 87221168, compound

HRID 2278351Notes

Reaction equation

HRID 2278351 reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Si:8]([O:15][CH2:16][CH:17]=O)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>S([O-])([O-])(=O)=O.[Cu+2].C(Cl)Cl>[Si:8]([O:15][CH2:16]/[CH:17]=[N:7]/[S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

5

Reactant 2

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

Product 1

HCID 87221168HCID 87221168, compoundYield 115.5%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A three necked round bottom flask fitted with a mechanical stirrer, nitrogen inlet and temperature probe was charged with (S)-(−)-2-Methyl-2-Propanesulfinamide (113 g, 0.929 mol) and DCM (2.0 L) at RT (endotherm to 9° C.). Copper(II) Sulfate (309 g, 1.94 mol) was then added followed by (tert-butyldimethylsilyl-oxy)acetaldehyde (150 g, 0.774 mol). After 36 hours the reaction was filtered through a plug of Celite, plug rinsed with DCM (3×200 mL), and concentrated to provide 248 g of the title compound as a light yellow syrup (87 wt %). 1H NMR (CDCl3) δ 8.08 (1H, s), 4.56 (2H, s), 1.22 (9H, s), 0.95 (9H, s), 0.12 (6H, s).

Workup

  1. customA three necked round bottom flask fitted with a mechanical stirrer, nitrogen inlet
  2. filtrationAfter 36 hours the reaction was filtered through a plug of Celite, plug
  3. washrinsed with DCM (3×200 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1e64df9f7c014fecb6e7bdd17a65a13d
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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