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Propargyl alcohol → Isohexane ethyl acetate

HRID 1444043
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HRID 1444043 반응식
Br[C:2]1[N:3]=[C:4]([O:28][CH3:29])[C:5]([N:8](COCC[Si](C)(C)C)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])(=[O:11])=[O:10])=[N:6][CH:7]=1.[CH2:30]([OH:33])[C:31]#[CH:32].[CH2:34](N([CH2:39][CH3:40])CC)C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:30]([O:33][CH2:39][CH3:40])(=[O:10])[CH3:31].[CH3:12][CH2:17][CH2:16][CH:15]([CH3:14])[CH3:34].[Cl:19][C:13]1[C:14]([Cl:18])=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([NH:8][C:5]1[C:4]([O:28][CH3:29])=[N:3][C:2]([C:32]#[C:31][CH2:30][OH:33])=[CH:7][N:6]=1)(=[O:10])=[O:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 59168156N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide

생성물 2

HCID 21882781Isohexane ethyl acetateHCID 591681002,3-Dichloro-N-[5-(3-hydroxy-1-propynyl)-3-methoxy-2-pyrazinyl]benzenesulphonamide

시약·촉매·용매 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418476HCID 178418476, 화합물촉매

실험 절차

A mixture of N-(5-bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide (Example 55a) (0.52 g), propargyl alcohol (0.223 mL), copper(I)iodide (0.05 g) and bis(triphenylphosphine)palladium(II) chloride (0.1 g) in triethylamine (3 mL) was stirred at room temperature and under nitrogen for 16 h. The solvent was evaporated. Chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures gave the title compound containing the SEM ([2-(trimethylsilyl)ethoxy]methyl) protecting group (0.38 g). 0.074 g of this compound was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (2 mL). After 1 h the solvent was evaporated. Chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures gave the title compound (0.043 g).

후처리

  1. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-d71187e891654376be20771b673cd87e
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07662825B2

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