Toluene → methyl delta-oxo-2-[5-[(tetrahydro-2H-pyran-2-yl)oxyl]-1E,3E-tridecadienyl]benzenepentanoate

HRID 1722339노트

반응식

HRID 1722339 반응식
C1(C)C=CC=CC=1.Br/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](=[O:25])[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22].C([Sn](CCCC)(CCCC)/[CH:31]=[CH:32]/[CH:33]([O:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][O:44]1)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])CCC.C(OCC)C>CCCCCC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[O:25]=[C:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1/[CH:10]=[CH:9]/[CH:31]=[CH:32]/[CH:33]([O:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][O:44]1)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 14582852methyl 2-(2-bromo-E-ethenyl)-delta-oxobenzenepentanoateHCID 14582853tetrahydro-2-[[1-[2-(tributylstannyl)-E-ethenyl]nonyl]oxy]-2H-pyran

생성물 1

HCID 14582854methyl delta-oxo-2-[5-[(tetrahydro-2H-pyran-2-yl)oxyl]-1E,3E-tridecadienyl]benzenepentanoate수율 50%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8058Hexane용매

실험 절차

To 1ml of toluene was added 0.1g (0.35 mol) of the product of Example 4, 0.11g (0.38 mmol) of the product of Example 9, and 5.0mg of tetrakis(triphenylphosphine)palladium(O). The solution was degassed with argon and then heated at reflux under argon for approximately 5 hours. The reaction mixture was then cooled to room temperature and flash chromatographed. Gradient elution with hexane, 1% diethyl ether in hexane, 5% diethyl ether in hexane, and 10% diethyl ether in hexane produced 0.90mg (0.19 mmol) of the titled product.

후처리

  1. customThe solution was degassed with argon
  2. temperatureheated
  3. temperatureat reflux under argon for approximately 5 hours
  4. customflash chromatographed
  5. washGradient elution with hexane, 1% diethyl ether in hexane, 5% diethyl ether in hexane

출처 및 근거

ORD 기록
ord-84834f24d5084fb7913e347b13a87eab
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04855324

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