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

HRID 1707402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1707402
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f88104559eef4de688002e3c7ad7a555
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05352820

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