Water → HCID 68868874, compound

HRID 1988226Notes

Reaction equation

HRID 1988226 reaction equation
[CH3:1][CH:2]([O:12][C:13](=[O:32])[C:14]1[C:19](OS(C(F)(F)F)(=O)=O)=[CH:18][C:17]([O:28][CH3:29])=[CH:16][C:15]=1[O:30][CH3:31])[CH2:3][CH2:4][C:5](=[O:11])[CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].[Cl-].[Li+].[CH:35]([Sn](CCCC)(CCCC)CCCC)=[CH2:36].O>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][CH:2]([O:12][C:13](=[O:32])[C:14]1[C:19]([CH:35]=[CH2:36])=[CH:18][C:17]([O:28][CH3:29])=[CH:16][C:15]=1[O:30][CH3:31])[CH2:3][CH2:4][C:5](=[O:11])[CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10]

Participants

7

Reactant 4

HCID 962WaterHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 86601652HCID 86601652, compound

Product 1

HCID 68868874HCID 68868874, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-dimethoxy-6-trifluoromethanesulfonyloxy-benzoic acid 1-methyl-4-oxo-non-8-enyl ester (0.041 g, 0.085 mmol), PdCl2(PPh3)2 (0.007 g, 0.01 mmol), lithium chloride (0.052 g, 1.2 mmol), and vinyltributyltin (50 μL, 0.17 mmol) in dimethylformamide (2 mL) was stirred at room temperature for 24 hours. After addition of water (10 mL), extraction, and chromatography afforded 2,4-dimethoxy-6-vinyl-benzoic acid 1-methyl-4-oxo-non-8-enyl ester as a clear oil (23 mg).

Sources & evidence

ORD record
ord-6cdfdf0ea343447abcfeff47fcf747af
Source dataset
uspto-grants-2009_06
Patent number
US07553979B2

Reaction notes

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