Hydrochloric Acid → HCID 13693403, Verbindung

HRID 846235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846235
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].Cl>C1COCC1.O>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH:10]([CH3:11])[CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 60984Methyl bromoacetateHCID 8211711-[4-(Methylthio)phenyl]-1-propanoneHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 13693403HCID 13693403, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The ketone from Step A (180 mg) in THF (2 ml) was added to a solution of lithium diisopropylamide (1.1 mmole) in THF (3 ml) at -78° under N2 atmosphere. After 15 minutes methyl bromoacetate (100 μl) was added and the mixture was warmed to ambient temperature and stirred 12 hours. The mixture was poured into water (15 ml) and conc. HCl (2 ml), extracted with CH2Cl2 and the extracts were dried (Na2SO4) evaporated to dryness and the residue purified by chromatography on silica gel to provide the title compound as an oil. NMR (CDCl3): 1.2 (3H, d), 2.55 (3H, s), 2.3-3.1 (2H, m), 3.65 (3H, s), 3.95 (1H, m), 7.3 (2H, d), 7.95 (2H, d).

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. dry with materialthe extracts were dried (Na2SO4)
  3. customevaporated to dryness
  4. customthe residue purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d453165e87fb4a34877f3cb13e11244f
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05135940

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