(3RS,4RS)-4-hydroxy-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran → (3RS,4RS)-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran

HRID 1859319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1859319
O[C:2]1([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)[C:7]2[CH:8]=[CH:9][C:10]([O:12][CH2:13][O:14][CH3:15])=[CH:11][C:6]=2[O:5][CH2:4][C:3]1([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][O:25][CH3:26])=[CH:19][CH:18]=1)[CH3:16]>CO.[Pd]>[OH:33][C:29]1[CH:28]=[C:27]([CH:2]2[C:7]3[CH:8]=[CH:9][C:10]([O:12][CH2:13][O:14][CH3:15])=[CH:11][C:6]=3[O:5][CH2:4][C:3]2([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][O:25][CH3:26])=[CH:21][CH:22]=2)[CH3:16])[CH:32]=[CH:31][CH:30]=1

Komponenten

4

Edukt 1

HCID 22123575(3RS,4RS)-4-hydroxy-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran

Produkt 1

HCID 22123578(3RS,4RS)-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyranAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

(3RS,4RS)-4-Hydroxy-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran (1.19 g, 2.63 mmol) prepared in Example 35 was dissolved in methanol (50 ml), and 10% Pd/C (200 mg) was slowly added dropwise thereto. The reaction mixture was stirred under hydrogen atmosphere for 12 hours and then filtered. The filtrate was concentrated under reduced pressure to remove the organic solvent. The concentrate was separated by column chromatography (n-hexane:ethyl acetate=8:1) to obtain 594 mg (yield: 50%) of the title compound as a colorless foam.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto remove the organic solvent
  4. customThe concentrate was separated by column chromatography (n-hexane:ethyl acetate=8:1)

Quellen und Nachweise

ORD-Eintrag
ord-2e1e1173b0914ae8bba9b8f307b31537
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06153768

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