Tetrahydrofuran → 2'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(2-propenyl)acetophenone

HRID 1030684노트

반응식

HRID 1030684 반응식
[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[CH2:10])=[C:6]([OH:11])[CH:5]=[C:4]([OH:12])[C:3]=1[C:13](=[O:15])[CH3:14].C(N(CC)C(C)C)(C)C.[CH3:25][O:26][CH3:27].[O:28]1[CH2:32]CC[CH2:29]1>>[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[CH2:10])=[C:6]([O:11][CH2:25][O:26][CH3:27])[CH:5]=[C:4]([O:12][CH2:29][O:28][CH3:32])[C:3]=1[C:13](=[O:15])[CH3:14]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 8254Dimethyl EtherHCID 81531DiisopropylethylamineHCID 143680782',4',6'-Trihydroxy3'-(2-propenyl)acetophenone

생성물 1

HCID 197448852'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(2-propenyl)acetophenone수율 94.7%

실험 절차

In 160 ml of anhydrous tetrahydrofuran were dissolved 18.4 g of the so-obtained 2',4',6'-trihydroxy3'-(2-propenyl)acetophenone and 57.1 g of N,N-diisopropylethylamine, and 28.4 g of chrolomethyl methyl ether was added to the solution under ice cooling and the reaction mixture was stirred under ice cooling for 1 hour, and further, stirred at room temperature for 4 hours to effect a reaction. The reaction mixture was extracted with diethyl ether and filtered, and the solvent was removed from the filtrate by distillation. The obtained residue was subjected to the silica gel column chromatography [eluting solvent=n-hexane/ethyl acetate (7/1)] to obtain 24.8 g (yield=94.7%) of 2'-hydroxy-4',6'-bismethoxymethoxy-3'-(2-propenyl)acetophenone in the form of a colorless oil.

후처리

  1. additionwas added to the solution under ice cooling
  2. stirringfurther, stirred at room temperature for 4 hours
  3. customa reaction
  4. extractionThe reaction mixture was extracted with diethyl ether
  5. filtrationfiltered
  6. customthe solvent was removed from the filtrate by distillation
  7. washThe obtained residue was subjected to the silica gel column chromatography [eluting solvent=n-hexane/ethyl acetate (7/1)]

출처 및 근거

ORD 기록
ord-7a22d84775e5409a8259bce92fa8e549
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05106871

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