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

HRID 1359145노트

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HRID 1359145 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
0 °C

실험 절차

The compound from Step C was mixed with 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. AlCl3 (2.3 g, 17.3 mmol) was added and the reaction stirred at room temperature overnight. 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, d, ArH), 8.02 (1H, d, ArH), 8.11 (1H, d, ArH), 8.41 (1H, d, ArH), 8.91 (1H, s, ArH).

후처리

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

출처 및 근거

ORD 기록
ord-f313c1aa751d4e14a2f724ef770a17fb
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599921B2

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