Ethylene Glycol → 3-Methoxy-8-(2-methyl-[1,3]-dioxolan-2-yl)-benzo[c]chromen-6-one

HRID 1359146ノート

反応式

HRID 1359146 の反応式
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[O:10][C:9](=[O:19])[C:8]=2[CH:20]=1)(=[O:3])[CH3:2].[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]3[CH:6]=[CH:5][C:4]([C:1]4([CH3:2])[O:23][CH2:22][CH2:21][O:3]4)=[CH:20][C:8]=3[C:9](=[O:19])[O:10]2)=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 103332378-Acetyl-3-methoxy-benzo[c]chromen-6-one

生成物 1

HCID 113244043-Methoxy-8-(2-methyl-[1,3]-dioxolan-2-yl)-benzo[c]chromen-6-one収率 60.7%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

The compound from Step D (5.2 g, 19 mmol), ethylene glycol (4.4 g, 71 mmol) and a catalytic amount of p-toluenesulfonic acid (0.2 g) were dissolved in benzene (300 ml) and refluxed for 28 h. The solvent was removed and the crude product chromatographed on silica gel with hexane/ethyl acetate (2:1) to yield 3.6 g (60%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 1.75 (3H, s, CH3), 3.82 (2H, t, OCH2), 3.91 (3H, s, OCH3), 4.10 (2H, t, OCH2), 6.93 (1H, s, ArH), 6.98 (1H, d, ArH), 7.47 (3H, m, ArH), 8.04 (1H, s, ArH).

後処理

  1. temperaturerefluxed for 28 h
  2. customThe solvent was removed
  3. customthe crude product chromatographed on silica gel with hexane/ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-13cd430abaf24388a0b139fb6bd04429
出典データセット
uspto-grants-2003_07
特許番号
US06599921B2

反応ノート

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