Hexane → Ethyl 5-Hydroxy-4-methyl-7-(1-methyl-4-phenylbutyl)coumarin-3-propionate

HRID 1389184

反応式

HRID 1389184 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10])[CH:5]=[C:6]([OH:8])[CH:7]=1.[CH3:20][CH2:21][O:22][C:23]([CH2:25][CH2:26][CH:27]([C:31](OCC)=[O:32])[C:28]([CH3:30])=O)=[O:24].P(Cl)(Cl)(Cl)=O.CCCCCC>C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:10])[CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[C:6]2[C:7]=1[C:28]([CH3:30])=[C:27]([CH2:26][CH2:25][C:23]([O:22][CH2:21][CH3:20])=[O:24])[C:31](=[O:32])[O:8]2

参加物

6

反応物 4

HCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 73915Diethyl 2-acetylglutarateHCID 204873675-(5-Phenylpentan-2-yl)benzene-1,3-diol

生成物 1

HCID 53719146Ethyl 5-Hydroxy-4-methyl-7-(1-methyl-4-phenylbutyl)coumarin-3-propionate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A mixture of 2-(3,5-dihydroxyphenyl)-5-phenylpentane (33 g., 0.13 M), (Preparation C) diethyl α-acetoglutarate (32.2 g., 0.14 M) and phosphorous oxychloride (20 g., 0.13 M), protected from atmospheric moisture, is stirred at room temperature. After 10 days, the mixture is dissolved in chloroform, washed three times with water, dried (Na2SO4), and evaporated. The residue is subjected to silica gel chromatography (eluents--9 benzene:1 ether) to yield 22 g. of the desired ester, m.p. 58°-70° C. from hexane. Further recrystallization from ethyl acetate/hexane affords an analytical sample: m.p. 78°-85° C.

後処理

  1. washwashed three times with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto yield 22 g
  5. customFurther recrystallization from ethyl acetate/hexane
  6. customaffords an analytical sample

出典と根拠

ORDレコード
ord-0decae391ec24e7f9a84a79f28035cc6
出典データセット
uspto-grants-1981_01
特許番号
US04243674

関連ノート

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