Diethyl 2-benzylpropanedioate → 2-Benzylpropane-1,3-diol

HRID 741545

Reaktionsgleichung

Reaktionsgleichung von HRID 741545
[CH2:1]([CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:1]([CH:8]([CH2:9][OH:10])[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 69090Diethyl 2-benzylpropanedioateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 5202412-Benzylpropane-1,3-diol

Versuchsvorschrift

Accordingly, diethyl benzylmalonate (1) is reduced with lithium aluminum hydride to afford 2-benzyl-1,3-propanediol (2) which is treated with an equimolar amount of tert-butyldimethylsilyl chloride to give the monoprotected alcohol 3. Swern (dimethylsulfoxide/oxalyl chloride) oxidation of 3 provides the aldehyde 4 which is condensed with the Wittig reagent methyl (triphenylphosphonylidene) acetate to give 6. Conversion of the alcohol 6 to the mesylate 7 followed by azide displacement affords 8 which is sequentially reduced and Boc protected to give 9. Jones oxidation of the tert-butyldimethylsilyl ether 9 provides the Boc protected substituted ω-aminoalkenoic acid 10.

Quellen und Nachweise

ORD-Eintrag
ord-3336992df8f542dc842e8ce196bb669e
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552383

Verknüpfte Notizen

Wird geladen…