2-Methoxybenzene-1,4-diol → 2,5,8-Trimethoxy-4a,9,9a,10-tetrahydro-9,10-[1,2]benzenoanthracene-1,4-dione

HRID 2306906

Reaktionsgleichung

Reaktionsgleichung von HRID 2306906
[CH3:1][O:2][C:3]1[C:16]2[C:7](=[CH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([O:17][CH3:18])=[CH:5][CH:4]=1.[CH3:19][O:20][C:21]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:22]=1[OH:23]>C1(C)C=CC=CC=1>[CH3:18][O:17][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:16]2[C:7]=1[CH:8]1[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]2[CH:24]2[C:22]([C:21]([O:20][CH3:19])=[CH:27][C:26](=[O:28])[CH:25]12)=[O:23]

Komponenten

4

Edukt 2

HCID 699882-Methoxybenzene-1,4-diolHCID 831071,4-Dimethoxyanthracene

Produkt 1

HCID 226299862,5,8-Trimethoxy-4a,9,9a,10-tetrahydro-9,10-[1,2]benzenoanthracene-1,4-dioneAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 0.70 g (2.90 mmol) of 2 and 1.00 g (7.20 mmol) of 6 in 10 mL of toluene in a sealed tube was heated at 150° C. for 1 day, cooled to 25° C., concentrated to dryness, and column chromatographed on silica gel using a gradient mixture of hexane and ethyl acetate as solvent gave 0.52 g (48% yield) of compounds 5 as a mixture of exo- and endo-(1:1) isomers along with 0.62 g of 6. The exo- and endo-isomers were partially separated by silica gel column and the stereochemistry have not assigned. Compound 5, less polar isomer: MS, m/z 376 (M+), 375. 1H NMR d 7.24-7.18 (m, 2H), 7.08-7.04 (m, 2H), 6.65 (s, 2H, C6,7 Hs), 5.61 (s, 1H), 5.33 (bs, 2H), 3.82 (s, 6H, OMe), 3.48 (s, 3H, OMe), 3.12 (ABd, J=9 Hz, 1H), 3.06 (ABd, J=9 Hz, 1H). More polar isomer: MS, m/z 376 (M+), 375. 1H NMR d 7.40 (m, 2H), 7.16 (m, 2H), 6.60 (ABd, J=8.8 Hz, 1H), 6.56 (Abd, J=8.8 Hz, 1H), 5.65 (s, 1H, ═CH), 5.33 (bs, 2H, C9,10 Hs), 3.76 (s, 3H, OMe), 3.73 (s, 3H, OMe), 3.51 (s, 3H, OMe), 3.13 (Abd, J=9 Hz, 1H), 3.08 (Abd, J=9 Hz, 1H). This mixture of compounds was used in the next step.

Aufarbeitung

  1. concentrationconcentrated to dryness, and column
  2. customchromatographed on silica gel using
  3. additiona gradient mixture of hexane and ethyl acetate as solvent

Quellen und Nachweise

ORD-Eintrag
ord-5e45cc1ea98e4902b7704c132fe8fe70
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06828450B2

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