Tributylvinyltin → HCID 19372293, compound

HRID 129694Notes

Reaction equation

HRID 129694 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[CH:10]=[C:9]([C:25]([O:27][CH3:28])=[O:26])[CH:8]=1)(=O)=O.[Li+].[Cl-].[CH:33]([Sn](CCCC)(CCCC)CCCC)=[CH2:34]>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:33]([C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:15]=2)[CH:10]=[C:9]([C:25]([O:27][CH3:28])=[O:26])[CH:8]=1)=[CH2:34]

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 19372372HCID 19372372, compound

Product 1

HCID 19372293HCID 19372293, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.5 g (1.4 mmol) of 1-trifluoromethylsulfonyloxy-3-carbomethoxy-6-benzyloxynaphthalene in 20 ml of DMF is stirred at 25° C. for 18 hours with 0.18 g (4.27 mmol, 3 eq) of LiCl, 0.46 ml (1.57 mmol, 1.1 eq) of vinyl-tributyltin and 0.019 g (0.03 mmol, 0.02 eq) bis(triphenyl-phosphine) palladium (II) chloride. The mixture is partitioned between ethyl acetate and 1N HCl. The organics are dried (MgSO4) and concentrated in vacuo. Purification by flash silica gel chromatography using 5% ethyl acetate in hexanes as an eluent affords 0.3 g of 1-vinyl-3-carbomethoxy-6-benzyloxynaphthalene in the form of a yellow oil which is used directly in the next step.

Workup

  1. customThe mixture is partitioned between ethyl acetate and 1N HCl
  2. dry with materialThe organics are dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-647613d400ae4b25a0f41ce5c503bf08
Source dataset
uspto-grants-1995_11
Patent number
US05468898

Reaction notes

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