Water → HCID 59511062, Verbindung

HRID 1157093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157093
[N:1]([CH:4]([CH2:7][OH:8])[CH2:5][OH:6])=[N+:2]=[N-:3].C([C:11](CC)(CC)[C:12]([O-])([O-])[O-:13])C.O.CCOC(C)=O>C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:12]([O:6][CH2:5][CH:4]([N:1]=[N+:2]=[N-:3])[CH2:7][OH:8])(=[O:13])[CH3:11]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 20578392HCID 20578392, VerbindungHCID 21875354Triethylorthoaceate

Produkt 1

HCID 59511062HCID 59511062, VerbindungAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Azidopropane-1,3-diol 23 (10.46 g, 89.3 mmol) was dissolved in CH2Cl2 (450 mL) and treated with a catalytic amount of p-toluene sulfonic acid monohydrate (340 mg, 1.8 mmol) and triethylorthoacetate (24.4 mL, 134 mmol) at room temperature for 1 hr. After the formation of the orthoester was complete, a stoichiometric amount of water (2.4 mL, 134 mmol) was added to the mixture. The mixture was then stirred for 40 min and then concentrated in vacuo. Purification of the residue on a silica gel cartridge using EtOAc:Hex as the eluent (5% EtOAc to 100% EtOAc) afforded 8.14 g (57% yield) of 24 as a clear, colorless oil. 1H NMR (CDCl3, 400 MHz), δ: 2.45 (1H, br s), 2.12 (3H, s), 3.63-3.78 (3H, m), 4.20-4.30 (2H, m).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customPurification of the residue on a silica gel cartridge

Quellen und Nachweise

ORD-Eintrag
ord-b41c88cbe3064d109a238904d26ca606
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807394B2

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