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

HRID 987590노트

반응식

HRID 987590 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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-129d764ffde641419e1eb6826055cef4
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06632835B2

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