Iodine → 4-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid methyl ester

HRID 2081314ノート

反応式

HRID 2081314 の反応式
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1Br.C([Sn](CC[CH2:42][CH3:43])(CCCC)/C=C/[Sn](CCCC)(CCCC)CCCC)CCC.[I:44]I>C1(C)C=CC=CC=1.C(OCC)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:43]=[CH:42]/[I:44]

参加物

7

反応物 3

HCID 807IodineHCID 5378370trans-1,2-Bis(tri-n-butylstannyl)ethyleneHCID 150701264-(2-Bromophenoxy)-butyric acid methyl ester

生成物 1

HCID 150701274-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid methyl ester収率 65.5%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

Under the conditions of example 2C, 482 mg of 4-(2-bromophenoxy)-butyric acid methyl ester and 3.2 g of (E)-1,2-bis-(tri-n-butylstannyl)-ethylene (50%) in 6 ml of toluene are heated in the presence of 47 mg of tetrakis-(triphenylphosphine)-palladium, diluted with 6 ml of diethyl ether, mixed with a solution of 1.02 g of iodine in 5 ml of diethyl ether, concentrated by evaporation, and the residue is chromatographed on silica gel. 400 mg of 4-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid methyl ester is obtained as an oily crude product, which is used in the next stage without further purification.

後処理

  1. concentrationconcentrated by evaporation
  2. customthe residue is chromatographed on silica gel

出典と根拠

ORDレコード
ord-646e1bbdca9643b2846206a3487de3c0
出典データセット
uspto-grants-1993_02
特許番号
US05183925

反応ノート

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