Triethylsilane → 5-(2-Benzyloxy-4-hydroxymethylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 660542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660542
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N:17]1[CH2:21][C:20](=[O:22])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[S:18]1(=[O:30])=[O:29])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:14]=[CH:15][C:16]=1[N:17]1[S:18](=[O:30])(=[O:29])[N:19]([CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[C:20](=[O:22])[CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 12052TriethylsilaneHCID 866250473-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde

Produkt 1

HCID 667566545-(2-Benzyloxy-4-hydroxymethylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde (1.6 g, 3.6 mmol) in benzene (20 mL), in a pressure vessel, is added triethylsilane (688 μL, 4.3 mmol) and (PPh3)2Re(O)2I (63 mg, 0.072 mmol). The vessel is sealed and the reaction is stirred at 60° C. for 18 h. The reaction is allowed to cool to RT and the solvent is removed under reduced pressure. The crude triethylsilyl ether is immediately dissolved in MeOH (20 mL), treated with TFA (approximately 0.15 mL) and stirred for 1 h. The solvent is removed under reduced pressure and the crude alcohol is purified by silica gel chromatography using a gradient of 0-50% EtOAc/hexane as eluent to afford the title compound as a light grey solid: (M+H)+=466.

Aufarbeitung

  1. customThe vessel is sealed
  2. temperatureto cool to RT
  3. customthe solvent is removed under reduced pressure
  4. dissolutionThe crude triethylsilyl ether is immediately dissolved in MeOH (20 mL)
  5. additiontreated with TFA (approximately 0.15 mL)
  6. stirringstirred for 1 h
  7. customThe solvent is removed under reduced pressure
  8. customthe crude alcohol is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-866dddd1c4e44ce0b4edfbce5ae49412
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084448B2

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