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

HRID 1707402ノート

反応式

HRID 1707402 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f88104559eef4de688002e3c7ad7a555
出典データセット
uspto-grants-1994_10
特許番号
US05352820

反応ノート

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