Ethanethiol → 1-Adamantyl (Ethylthio)methyl Ketone

HRID 34742

Reaktionsgleichung

Reaktionsgleichung von HRID 34742
[CH2:1]([SH:3])[CH3:2].C([Li])CCC.Br[CH2:10][C:11]([C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:12]>C1COCC1>[CH2:1]([S:3][CH2:10][C:11]([C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:12])[CH3:2]

Komponenten

5

Edukt 3

HCID 6343EthanethiolHCID 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketoneHCID 178418339Butyllithium

Produkt 1

HCID 538821091-Adamantyl (Ethylthio)methyl Ketone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

Ethyl mercaptan (5.76 ml., 4.83 g., 0.078 mol) in 250 ml. THF was cooled to -70°. n-Butyllithium (50 ml. of 1.55M in hexane, 0.078 mol) was added over 10 minutes at that temperature. The mixture was then allowed to warm to 10°, recooled to -70°, and 1-adamantyl bromomethyl ketone (20 g., 0.078 mol) in 125 ml. THF added over. The mixture was stirred 15 minutes at -70° C., stripped to one fifth volume, diluted to 600 ml. with ether, washed 2×200 ml. saturated NH4Cl, 3×150 ml. H2O and 1×200 ml. brine, dried over MgSO4 and stripped to yield title product as an oil, 18.5 g. 1H-nmr (300 MHz) 1.2 (t, 3H), 1.6-2.1 (m, 15H), 2.5 (q, 2H), 3.35 (s, 2H).

Aufarbeitung

  1. temperatureto warm to 10°
  2. customrecooled to -70°
  3. additiondiluted to 600 ml
  4. washwith ether, washed 2×200 ml
  5. dry with materialbrine, dried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-34f01fc627254bcf8470d76189645de3
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762921

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