Dimethyl Sulfoxide → 3-o-t-Butyldimethylsilyl-2-o-methyl-rac-glyceraldehyde

HRID 496999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 496999
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][CH2:19][CH:20]([CH2:23][OH:24])[O:21][CH3:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[Si:11]([O:18][CH2:19][CH:20]([O:21][CH3:22])[CH:23]=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 223164511-o-t-Butyldimethylsilyl-2-o-methyl-rac-glycerol

Produkt 1

HCID 543075043-o-t-Butyldimethylsilyl-2-o-methyl-rac-glyceraldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of oxalyl chloride (87 μL, 1.0 mmol) in CH2Cl2 (7 mL) at −78° C. was added DMSO (71 μL, 1.0 mmol). After 20 min, alcohol Compound 42 (0.20 g, 0.91 mmol) was added followed, after another 20 min, by the addition of triethylamine (0.63 mL, 4.6 mmol). The reaction was warmed to room temperature over a 10 min period, filtered through a plug of silica-gel, which was washed with ethyl acetate (50 mL) and concentrated to give 3-O-t-butyldimethylsilyl-2-O-methyl-rac-glyceraldehyde Compound 73 (0.20 g, 100%) as a colourless oil.

Aufarbeitung

  1. filtrationfiltered through a plug of silica-gel, which
  2. washwas washed with ethyl acetate (50 mL)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d8dfd62967db42498476675a65d5d555
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949529B2

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