HCID 18436361, Verbindung → [6-Hydroxymethyl-3,4-bis-(4-methoxy-phenyl)-cyclohex-3-enyl]-methanol

HRID 351447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351447
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH:11]3[CH:15]([CH2:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:14](=O)[O:13][C:12]3=[O:27])=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:27][CH2:12][CH:11]1[CH:15]([CH2:14][OH:13])[CH2:16][C:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10]1

Komponenten

4

Edukt 2

HCID 18436361HCID 18436361, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 18436365[6-Hydroxymethyl-3,4-bis-(4-methoxy-phenyl)-cyclohex-3-enyl]-methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To the cooled solution of 5,6-bis-(4-methoxy-phenyl)-3a,4,7,7a-tetrahydro-isobenzofuran-1,3-dione (2.95g) in THF (30 mL) at 0° C. was added LAH (1.0 M in THF, 20 mL) and the reaction mixture was stirred at 25° C. for 16. The reaction mixture was then quenched with methanol (20 mL) and aqueous HCl (10%, 30 mL) and then extracted with diethyl ether (2×300 mL). The organic layer was dried and concentrated to yield [6-Hydroxymethyl-3,4-bis-(4-methoxy-phenyl)-cyclohex-3-enyl]-methanol.

Aufarbeitung

  1. customThe reaction mixture was then quenched with methanol (20 mL) and aqueous HCl (10%, 30 mL)
  2. extractionextracted with diethyl ether (2×300 mL)
  3. customThe organic layer was dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a284c620b48e4bbfaa0ccb0534fecb54
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183445B2

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