Lithium Hydroxide → 1-(5-Ethynyl-2-thienyl)-2,2,2-trifluoroethanone

HRID 1715350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1715350
[F:1][C:2]([F:17])([F:16])[C:3]([C:5]1[S:6][C:7]([C:10]#[C:11][Si](C)(C)C)=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[C:10]([C:7]1[S:6][C:5]([C:3](=[O:4])[C:2]([F:1])([F:17])[F:16])=[CH:9][CH:8]=1)#[CH:11]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 685070782,2,2-Trifluoro-1-{5-[(trimethylsilyl)ethynyl]-2-thienyl}ethanone

Produkt 1

HCID 576201031-(5-Ethynyl-2-thienyl)-2,2,2-trifluoroethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of D1 (1.0 eq) in THF (0.1 M) at RT was added a solution of LiOH (2.0 eq) in H2O (0.1 M) and the reaction mixture was stirred for 1 hr, then quenched by adding 6M HCl solution until pH=2. The organic solvent was evaporated and the product was extracted by DCM. Organic layers were washed with brine and dried (Na2SO4). Evaporation of the solvent under reduced pressure gave the crude product which was purified by flash column chromatography using Pentane to yield the desired compound as a brown oil. 1H NMR (300 MHz, CDCl3, 300K) δ 7.85-7.80 (1H, m), 7.32 (1H, d, J=4.2 Hz), 3.66 (1H, s).

Aufarbeitung

  1. customquenched
  2. additionby adding 6M HCl solution until pH=2
  3. customThe organic solvent was evaporated
  4. extractionthe product was extracted by DCM
  5. washOrganic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent under reduced pressure
  8. customgave the crude product which
  9. customwas purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-21d3111858bb4bc586bc5bdd9f69c1fe
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799825B2

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