Thionyl Chloride → 8-Acetyl-3-methoxy-benzo[c]chromen-6-one

HRID 987590ノート

反応式

HRID 987590 の反応式
[C:1]([C:4]1[CH:5]=[C:6]([C:20]([OH:22])=[O:21])[C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2OC)=[CH:8][CH:9]=1)(=[O:3])[CH3:2].O=S(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[C:1]([C:4]1[CH:9]=[CH:8][C:7]2[C:10]3[C:11](=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[O:22][C:20](=[O:21])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 113471004-Acetyl-2',4'-dimethoxy-biphenyl-2-carboxylic acid

生成物 1

HCID 103332378-Acetyl-3-methoxy-benzo[c]chromen-6-one収率 90%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

The compound from Step D was dissolved in 1,2-dichloroethane (60 mL) and SOCl2 (1.7 mL, 23 mmol) was added. The mixture was refluxed for 90 min and then cooled to 0° C. at which point AlCl3 (2.3 g, 17.3 mmol) was added. The resulting reaction mixture was stirred overnight at room temperature. The solvent was removed and the crude product chromatographed on silica gel with hexane/ethyl acetate (1:1) to yield 5.1 g (90%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 2.74 (3H, s, COCH3), 3.94 (3H, s, OCH3), 6.92 (1H, s, ArH), 6.99 (1H, ArH), 8.02 (1H, d, ArH), 8.11 (1H, d, ArH), 8.41 (1H, d, ArH), 8.91 (1H, s, ArH).

後処理

  1. temperatureThe mixture was refluxed for 90 min
  2. additionwas added
  3. customThe resulting reaction mixture
  4. customThe solvent was removed
  5. customthe crude product chromatographed on silica gel with hexane/ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-129d764ffde641419e1eb6826055cef4
出典データセット
uspto-grants-2003_10
特許番号
US06632835B2

反応ノート

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