Furfuryl Alcohol → (1RS,2SR,6RS,7SR)-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-ene-3,5-dione

HRID 407861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407861
[CH2:1]([OH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[CH:17]1[C:21](=[O:22])[CH:20]=[CH:19][C:18]1=[O:23].[Mg+2].[I-].[I-]>>[OH:7][CH2:1][C:2]12[O:6][CH:5]([CH:4]=[CH:3]1)[CH:19]1[CH:20]2[C:21](=[O:22])[CH:17]([C:10]2[C:11]([CH3:16])=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=2[CH3:8])[C:18]1=[O:23]

Komponenten

4

Edukt 3

HCID 7361Furfuryl AlcoholHCID 5462737Magnesium diiodideHCID 666844242-(2,4,6-Trimethylphenyl)cyclopent-4-ene-1,3-dione

Produkt 1

HCID 67284116(1RS,2SR,6RS,7SR)-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-ene-3,5-dione

Versuchsvorschrift

Furfuryl alcohol (4 ml, 46.7 mmol) is added to 2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione (2.0 g, 9.3 mmol) and MgI2 (520 mg, 1.86 mmol) and the reaction is stirred for 17 hours. The reaction mixture is adsorbed onto silica gel and purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-ene-3,5-dione.

Aufarbeitung

  1. custompurified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1499e149ff694596b41c4a4955c9b88b
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754242B2

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