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

HRID 1722339ノート

反応式

HRID 1722339 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-84834f24d5084fb7913e347b13a87eab
出典データセット
uspto-grants-1989_08
特許番号
US04855324

反応ノート

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