Cyclohexene, 1-((trimethylsilyl)oxy)- → beta(R)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-ethanol

HRID 376004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 376004
[CH2:1]([O:8][C@@H:9]([C@H:12]([OH:15])[CH2:13][OH:14])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1(O[Si](C)(C)C)[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=1>C(OCC)C.Cl>[CH2:1]([O:8][C@@H:9]([C@H:12]1[CH2:13][O:14][C:16]2([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[O:15]1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 81161Cyclohexene, 1-((trimethylsilyl)oxy)-HCID 10867592(2R,3R)-(-)-2-Benzyloxy-1,3,4-butanetriol

Produkt 1

HCID 53702433beta(R)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-ethanolAusbeute 96.624,102 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

4.34 g (0.02 mol) of (2R,3R)-2-benzyloxybutane-1,3,4-triol were suspended in a mixture of 3.4 g (0.02 mmol) of 1-cyclohexenyloxytrimethylsilane and 40 ml of diethyl ether. Two drops of concentrated hydrochloric acid were added and the mixture was stirred at room temperature for 30 minutes. The mixture was then evaporated to give 5.65 g of β(R)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-ethanol in the form of a colourless viscous oil; MS: m/e 292 [M]+.

Aufarbeitung

  1. customThe mixture was then evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b6b2329048bf4e38843d8e433579907f
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488115

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