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

HRID 2306906

반응식

HRID 2306906 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5e45cc1ea98e4902b7704c132fe8fe70
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828450B2

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