Sodium Bicarbonate → 3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde

HRID 1642610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1642610
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:15]=C)[CH:12]=[CH:11][C:10]=1[N:17]1[S:21](=[O:23])(=[O:22])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:19](=[O:30])[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[O:34]CC1.CC(O)(C)C.O.C([O-])(O)=O.[Na+]>CC(O)(C)C.O.O=[Os](=O)(=O)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=1[N:17]1[CH2:18][C:19](=[O:30])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:27])[CH3:28])[S:21]1(=[O:23])=[O:22])[CH:15]=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 22124471t-Butanol tetrahydrofuran waterHCID 667565425-(2-Benzyloxy-4-vinylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a solution of 5-(2-benzyloxy-4-vinylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (1.9 g, 4.3 mmol) in 1:1:1 THF/t-BuOH/H2O (60 mL) is added 1-methylmorpholine-N-oxide (551 mg, 4.74 mmol) and OsO4 (2 mL of a 2.5 wt % solution in t-BuOH, 0.17 mmol). The reaction is stirred for 4 h at ambient temperature, then diluted with water (15 mL) and treated with NaIO4 (4.5 g, 21.5 mmol) and NaHCO3 (3.6 g, 43 mmol). The mixture is stirred vigorously for 1 h, then filtered through Celite. The solution is extracted with EtOAc. The organic phase is washed with saturated NaCl. The solution is dried over MgSO4 and the solvent removed under reduced pressure, then purified via silica gel chromatography using a gradient of 0-40% EtOAc/hexanes to afford 3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde as a white solid: MS (M+NH4)+=464.

Aufarbeitung

  1. stirringThe mixture is stirred vigorously for 1 h
  2. filtrationfiltered through Celite
  3. extractionThe solution is extracted with EtOAc
  4. washThe organic phase is washed with saturated NaCl
  5. dry with materialThe solution is dried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. custompurified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d63d14fe92084c379acb0d6968bc796f
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119666B2

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