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Imidazole → (3-(tert-Butyl-dimethyl-silanyloxy)-prop-1-ynyl]-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1473247
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Reaktionsgleichung

Reaktionsgleichung von HRID 1473247
[OH:1][CH2:2][C:3]#[C:4][C:5]1[C:6]2[CH2:17][CH2:16][CH2:15][CH2:14][C:7]=2[S:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11].N1C=CN=C1.[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25].CCOC(C)=O>ClCCl>[CH3:13][O:12][C:10]([C:9]1[S:8][C:7]2[CH2:14][CH2:15][CH2:16][CH2:17][C:6]=2[C:5]=1[C:4]#[C:3][CH2:2][O:1][Si:27]([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28])=[O:11]
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Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 89463106Methyl 3-(3-hydroxyprop-1-yn-1-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylate

Produkt 1

HCID 89462605(3-(tert-Butyl-dimethyl-silanyloxy)-prop-1-ynyl]-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid methyl esterAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-(3-hydroxyprop-1-yn-1-yl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxylate (8.5 g, 34 mmol) in Dichloromethane (DCM) (50 mL) was added 1H-imidazole (5.8 g, 85 mmol) and TBSCl (7.7 g, 50.9 mmol). The mixture was stirred at room temperature for 2 h. The reaction mixture was washed with water, brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by chromatography column on silica gel chromatography eluted with PE:EtOAc=50:1˜20:1 to afford title product (11.9 g, 96% yield). 1HNMR: (400 MHz, CDCl3) δ 0.161 (s, 6H), 0.929 (s, 9H), 1.79-1.85 (m, 4H), 2.60-2.63 (m, 2H), 2.72-2.75 (m, 2H), 3.85 (s, 3H), 4.62 (s, 2H).

Aufarbeitung

  1. washThe reaction mixture was washed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by chromatography column on silica gel chromatography
  5. washeluted with PE

Quellen und Nachweise

ORD-Eintrag
ord-f2dcd186d6d242cfa5a3e2b9b1b6d441
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012642B2

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