Tributylvinyltin → 2-Methoxy-7-vinyl-naphthalene

HRID 1825045Notes

Reaction equation

HRID 1825045 reaction equation
[Li+].[Cl-].[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11](OS(C(F)(F)F)(=O)=O)=[CH:12]2)=[CH:7][CH:6]=1.[CH2:23]([Sn](CCCC)(CCCC)C=C)[CH2:24]CC>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>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:13](=[CH:12][C:11]([CH:23]=[CH2:24])=[CH:10][CH:9]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 10892112Methanesulfonic acid, trifluoro-, 7-methoxy-2-naphthalenyl ester

Product 1

HCID 221449672-Methoxy-7-vinyl-naphthaleneYield 97.8%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

To a mixture of (Ph3P)2PdCl2 (1.752 g), LiCl (6.36 g), and trifluoromethanesulfonic acid 7-methoxy-naphthalen-2-yl ester (15.3 g) was added dropwise tributyl(vinyl)tin (19.02 g). The resulting mixture was stirred over 4 h at 90° C. The reaction was quenched with water and extracted with CH2Cl2. The organic layer was washed with water and dried over MgSO4. After concentration, the crude product was purified by flash chromatography eluting with 20% ethyl acetate in hexanes to give the title compound as an oil (9 g).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationAfter concentration
  6. customthe crude product was purified by flash chromatography
  7. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ef4095385e1d466d89f26722f924be1f
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

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