Water → HCID 21255848, Verbindung

HRID 481720

Reaktionsgleichung

Reaktionsgleichung von HRID 481720
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][CH:12]2[O:16][C:15](=[O:17])[CH2:14][CH2:13]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C.O>C1(C)C=CC=CC=1>[OH:17][CH:15]1[CH2:14][CH2:13][CH:12]([CH2:11][O:10][S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:18])=[CH:6][CH:5]=2)(=[O:9])=[O:8])[O:16]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 4609541(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Produkt 1

HCID 21255848HCID 21255848, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a suspension of (±)-dihydro-5-(p-toluensulfonyloxymethyl)-2(3H)-furanone (example 57) (5.20 g, 19.26 mmol) in anhydrous toluene (125 mL) at -78° C. was added DIBAL (1.5M in toluene, 13.5 mL, 20.22 mmol) dropwise. The solution was allowed to stir at -78° C. for 2 h. Water was then added to the mixture and the reaction mixture was brought to rt. The mixture was filtered through Celite and the organic layer was collected, dried (MgSO4) and concentrated to give the title compound as a 1:1 mixture of cis and trans isomers (4.2 g, 80%).

Aufarbeitung

  1. customwas brought to rt
  2. filtrationThe mixture was filtered through Celite
  3. customthe organic layer was collected
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-130f7161d5024503a220617a495fe875
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789394

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