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Acetic Acid → Neo-tanshinlactone

HRID 1713712
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HRID 1713712 반응식
[OH:1][C:2]1[C:11]2[C:6](=[C:7]3[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:8]3=[CH:9][CH:10]=2)[O:5][C:4](=[O:17])[CH:3]=1.CC(O)=O.Cl[CH2:23][C:24](=O)[CH3:25]>C1(C)C=CC=CC=1.CCO.O>[CH3:16][C:12]1[C:8]2[CH:9]=[CH:10][C:11]3[C:2]4[O:1][CH:23]=[C:24]([CH3:25])[C:3]=4[C:4](=[O:17])[O:5][C:6]=3[C:7]=2[CH:15]=[CH:14][CH:13]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 176Acetic AcidHCID 6571ChloroacetoneHCID 547180894-Hydroxy-7-methyl-benzo[h]chromen-2-one

생성물 1

HCID 10264769Neo-tanshinlactone수율 60.2%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매
HCID 1140
Toluene
용매

실험 절차

To a solution of 7 (50 mg, 0.22 mmol) in toluene (8 mL) was added a mixture of HOAc (66 mg, 1.1 mmol) and NH4OAc (80 mg, 1.1 mmol) in EtOH (2 mL) and chloroacetone (103 mg, 1.1 mmol). The mixture was refluxed 24 h. After cooling, the mixture was diluted with H2O and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by column chromatography to give 1 (35 mg, 60%) as a white solid. The spectroscopic data of synthetic compound 1 were identical with those of the natural product 1.

후처리

  1. temperatureThe mixture was refluxed 24 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-b58374f484c5459caacaabe8951ef3f3
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795299B2

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