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

HRID 1722339Notes

Reaction equation

HRID 1722339 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8058HexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-84834f24d5084fb7913e347b13a87eab
Source dataset
uspto-grants-1989_08
Patent number
US04855324

Reaction notes

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