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

HRID 2081314노트

반응식

HRID 2081314 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-646e1bbdca9643b2846206a3487de3c0
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05183925

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