Tributylvinyltin → HCID 57424239, compound

HRID 2377385Notes

Reaction equation

HRID 2377385 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[C:21](OS(C(F)(F)F)(=O)=O)[C:20]3[C:19](=[O:31])[CH2:18][CH2:17][C:16]([CH3:33])([CH3:32])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1.[Cl-].[Li+].[CH2:37]([Sn](CCCC)(CCCC)C=C)[CH2:38]CC>CN1CCCC1=O.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>[CH3:1][O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:22]=[C:21]([CH:37]=[CH2:38])[C:20]3[C:19](=[O:31])[CH2:18][CH2:17][C:16]([CH3:32])([CH3:33])[C:15]=3[CH:14]=2)=[CH:9][CH:10]=1

Participants

8

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 57424238HCID 57424238, compound2×

Product 1

HCID 57424239HCID 57424239, compoundYield 86%

Reagents, catalysts & solvents 4

HCID 521585Tris(furan-2-yl)phosphaneCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of {4-[8,8-dimethyl-5-oxo-4-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-acetic acid methyl ester (Intermediate 69, 0.233 g, 0.47 mmol) in anhydrous 1-methyl 2-pyrrolidinone (3 mL) was sparged with argon, and treated with lithium chloride (0.061 g, 1.45 mmol), tri-2-furylphosphine (0.0071 g, 0.031 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.007 g, 0.015 mmol). After 5 minutes, tributyl(vinyl)tin (0.175 g, 0.55 mmol) was added and the resulting reaction mixture was stirred at ambient temperature for 2.5 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with brine and water, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column chromatography over silica gel (230-400 mesh) using 10-15% ethyl acetate in hexane as the eluent to afford the title compound (0.15 g, 86%) as a white solid.

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to a residue that

Sources & evidence

ORD record
ord-4758ce795ec74f219485234297420c76
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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