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

HRID 1030684ノート

反応式

HRID 1030684 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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)]

出典と根拠

ORDレコード
ord-7a22d84775e5409a8259bce92fa8e549
出典データセット
uspto-grants-1992_04
特許番号
US05106871

反応ノート

読み込み中…