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

HRID 1707402노트

반응식

HRID 1707402 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f88104559eef4de688002e3c7ad7a555
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05352820

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