Sodium Sulfite → 2-(t-Butoxycarbonylamino)-3-(t-butyldiphenylsiloxy)propanal

HRID 352868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 352868
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:12][O:13][Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:12][O:13][Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH:10]=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 227105032-(t-Butoxycarbonylamino)-3-(t-butyldiphenylsiloxy)propanol

Produkt 1

HCID 232404152-(t-Butoxycarbonylamino)-3-(t-butyldiphenylsiloxy)propanal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(t-butoxycarbonylamino)-3-(t-butyldiphenylsiloxy)propanol (3.03 g) in methylene chloride (100 ml), Dess-Martin periodinane (3.60 g) was added at room temperature. The resulting mixture was stirred for 30 minutes. To the reaction mixture, a saturated aqueous solution (50 ml) of sodium bicarbonate and a 10% aqueous solution (50 ml) of sodium sulfite were added to cause separation. The water layer was extracted with diethyl ether (50 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column (150 g of silica gel, hexane:ethyl acetate=4:1→3:1), whereby the title compound (2.97 g) was obtained as a colorless transparent oil.

Aufarbeitung

  1. customseparation
  2. extractionThe water layer was extracted with diethyl ether (50 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by chromatography on a silica gel column (150 g of silica gel, hexane:ethyl acetate=4:1→3:1), whereby the title compound (2.97 g)
  7. customwas obtained as a colorless transparent oil

Quellen und Nachweise

ORD-Eintrag
ord-575a5c2102364cfda3cf397f99b5b636
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747023B1

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