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

HRID 1389184

반응식

HRID 1389184 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0decae391ec24e7f9a84a79f28035cc6
출처 데이터셋
uspto-grants-1981_01
특허 번호
US04243674

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