(s)-(+)-5-[(1,1'-Biphenyl)-4-yl]-4-hydroxy-5-methyl-3-phenylmethoxy-2(5h)-furanone → (S)-(+)-5-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone

HRID 612568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612568
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([C@:7]2([CH3:22])[O:11][C:10](=[O:12])[C:9]([O:13]CC3C=CC=CC=3)=[C:8]2[OH:21])=[CH:3][CH:2]=1>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:1]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:6]=[CH:5][C:4]([C@:7]2([CH3:22])[O:11][C:10](=[O:12])[C:9]([OH:13])=[C:8]2[OH:21])=[CH:3][CH:2]=1

Komponenten

4

Edukt 1

HCID 70248116(s)-(+)-5-[(1,1'-Biphenyl)-4-yl]-4-hydroxy-5-methyl-3-phenylmethoxy-2(5h)-furanone

Produkt 1

HCID 70246787(S)-(+)-5-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanoneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 16218511Pd barium sulfateKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

The (S)-(+)-5-[(1,1'-biphenyl)-4-yl]-4-hydroxy-5-methyl-3-phenylmethoxy-2(5H)-furanone was subjected to hydrogenation over 100 mg of 5% Pd/BaSO4 in 100 mL of MeOH at room temperature under 30 psi of H2. The reaction was monitored periodically by TLC analysis. Upon reaction completion, the suspension was filtered through two #1 filter papers, concentrated and recrystallized from CHCl3 and hexanes to provide 300 mg (20% overall yield from methyl (S)-(+)-2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate) of (S)-(+)-5-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone as a light weight white crystalline material: mp 204-206° C. dec.; [α]25D +121° (c=0.66; MeOH); 1H NMR (acetone-d6) δ 7.72-7.41 (m, 9H), 1.89 (s, 3H). Anal Calcd for C17H14O4 +0.75 H2O: C, 69.03; H, 5.28. Found: C, 68.69; H, 4.95.

Aufarbeitung

  1. customUpon reaction completion
  2. filtrationthe suspension was filtered through two #1
  3. filtrationfilter papers
  4. concentrationconcentrated
  5. customrecrystallized from CHCl3 and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2e4818d340a846378c72ba7ac69d2e01
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06005000

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