Diethyl Ether → 6-Methoxy-alpha-methylene-2-naphthaleneacetic acid methyl ester

HRID 1707402Notes

Reaction equation

HRID 1707402 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6]2.[CH3:21][O:22][C:23](=[O:39])[C:24]([Sn](CCCC)(CCCC)CCCC)=[CH2:25].[Cl-].[Li+].C(OCC)C>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:21][O:22][C:23](=[O:39])[C:24](=[CH2:25])[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 433294Lithium ChlorideHCID 109597232-Propenoic acid, 2-(tributylstannyl)-, methyl esterHCID 117817166-Methoxynaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 101986916-Methoxy-alpha-methylene-2-naphthaleneacetic acid methyl esterYield 71%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a room temperature solution of 0.306 g of product from Example 9 in 10 ml of dimethylformamide is added 0.938 g of 2-(tributylstannyl)-2-propenoic acid methyl ester, 0.116 g of tetrakis(triphenylphosphine)palladium(0), 0.143 g of copper(1)iodide and 0.128 g of lithium chloride. The resulting reaction mixture is stirred, at room temperature, for 48 hours and then poured into 100 ml of diethyl ether. The layers are separate, the organic layer is washed with water and saturated sodium chloride, dried, filtered and concentrated in vacuo. The residue is purified by chromatography (silica gel: ethyl acetate/hexane 1/20) to give 0.171 g (71% yield) of the desired product as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. customThe layers are separate
  3. washthe organic layer is washed with water and saturated sodium chloride
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by chromatography (silica gel: ethyl acetate/hexane 1/20)

Sources & evidence

ORD record
ord-f88104559eef4de688002e3c7ad7a555
Source dataset
uspto-grants-1994_10
Patent number
US05352820

Reaction notes

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