Cesium carbonate → Methyl 5-((tert-butyldimethylsilyloxy)methyl)-3-phenylthiophene-2-carboxylate

HRID 1186711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186711
[Si:1]([O:8][CH2:9][C:10]#[C:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]([O:24][CH3:25])(=[O:23])[CH2:21][SH:22].S([O-])([O-])(=O)=O.[Mg+2].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.CO>[Si:1]([O:8][CH2:9][C:10]1[S:22][C:21]([C:20]([O:24][CH3:25])=[O:23])=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 16907Methyl ThioglycolateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 108695084-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one

Produkt 1

HCID 66863649Methyl 5-((tert-butyldimethylsilyloxy)methyl)-3-phenylthiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 167 (8.924 g, 32.5 mmol) in THF was added methyl thioglycolate (4.36 mL, 48.8 mmol) and stirred 2 hours at room temperature. MAGNESIUM SULFATE (3.91 g, 32.5 mmol) was added and the reaction mixture was stirred for 1 hour. Then CESIUM CARBONATE (10.60 g, 32.5 mmol) in 30 mL of MeOH was added and stirred for an additional 2 hours at room temperature. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with brine, dried over sodium sulfate and filtered. The solvent was evaporated and the residue was purified by silica gel chromatography (0%-5% ethyl acetate in hexanes) to yield 168 in 54% (6.389 g) as an orange solid

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 1 hour
  2. stirringstirred for an additional 2 hours at room temperature
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customThe solvent was evaporated
  10. customthe residue was purified by silica gel chromatography (0%-5% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-831f253868a741158a66a8f91f556976
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673911B2

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