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4-Methoxybenzaldehyde → (6-Methoxy-2-methylsulfanyl-quinolin-5-yl)-(4-methoxy-phenyl)methanol

HRID 1825860
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HRID 1825860 반응식
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:14][CH3:15])=[N:7]2.[Li]C(C)(C)C.[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1>C1COCC1.CCCCC>[CH3:13][O:12][C:11]1[C:2]([CH:27]([C:26]2[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[OH:28])=[C:3]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6]([S:14][CH3:15])[CH:5]=[CH:4]2
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참가 물질

6

반응물 3

HCID 312444-MethoxybenzaldehydeHCID 221396965-Bromo-6-methoxy-2-methylthioquinolineHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 22139702(6-Methoxy-2-methylsulfanyl-quinolin-5-yl)-(4-methoxy-phenyl)methanol수율 35%

시약·촉매·용매 2

HCID 8003Pentane용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

A solution of 280 mg (1 mmole) of 5-bromo-6-methoxy-2-methylsulfanyl-quinoline in 4 mL THF was cooled to −78° C. and treated with 1.5 mL of 1.5 M t-BuLi in pentane. After stirring for 1.5 hours, 1.5 eq of p-methoxybenzaldehyde was added and the reaction allowed to warm to room temperature. After partitioning between EtOAc and water the product was purified by chromatography on silica gel (1:3 EtOAc/hexane) to afford (6-methoxy-2-methylsulfanyl-quinolin-5-yl)-(4-methoxy-phenyl)methanol (120 mg, 35%).

후처리

  1. customAfter partitioning between EtOAc and water the product
  2. customwas purified by chromatography on silica gel (1:3 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-0997453f44da4df793eaca97507a9e3d
출처 데이터셋
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07049325B2

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