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Lithium Chloride → Ethyl [3-(pyridin-3-yl)phenyl]acetate

HRID 465514
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HRID 465514 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)(=O)=O.FC(F)(F)S(O[C:21]1[CH:22]=[C:23]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:24]=[CH:25][CH:26]=1)(=O)=O.C[Sn](C)C.C[Sn](C)C.[Cl-].[Li+]>[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>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:25]2[CH:24]=[C:23]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:22]=[CH:21][CH:26]=2)[CH:8]=1
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참가 물질

6

반응물 4

HCID 433294Lithium ChlorideHCID 6327618HexamethylditinHCID 110315793-Pyridyl TrifluoromethanesulfonateHCID 14986694HCID 14986694, 화합물

생성물 1

HCID 14986695Ethyl [3-(pyridin-3-yl)phenyl]acetate

시약·촉매·용매 1

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매

실험 절차

3-(Trifluoromethylsulfonyloxy)-pyridine is condensed with ethyl m-(trifluoromethanesulfonyloxy)-phenylacetate in the presence of hexamethylditin, lithium chloride and tetrakis-(triphenylphosphine)-palladium to obtain ethyl m-(3-pyridyl)-phenylacetate. The product is alkylated with 1-bromo-4-chlorobutane to obtain the alpha-(4-chlorobutyl)substituted phenylacetic acid ester. The ester is then reduced to the aldehyde which is condensed with e.g. methyl(triphenylphosphoranylidene)-acetate. The resulting alpha,beta-unsaturated ester is saturated to methyl 8-chloro-4-[m-(3-pyridyl)phenyl]-octanoate which is converted to methyl 8-amino-4-[m-(3-pyridyl)-phenyl]octanoate according to methodology described herein.

출처 및 근거

ORD 기록
ord-525f0ce577e649b4b479b60e7132c457
출처 데이터셋
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05153214

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