Dichloromethane → HCID 13349252, Verbindung

HRID 364334

Reaktionsgleichung

Reaktionsgleichung von HRID 364334
[Cl-].C([Al+][CH2:5][CH3:6])C.[CH2:7](Cl)Cl.CS(O[C@H]([C:17]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]C)([OH:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])C)(=O)=O>P(=O)(O)(O)O.C(OCC)(=O)C>[CH3:7][C@@H:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:5][CH3:6])[C:17](=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 13349246HCID 13349246, VerbindungHCID 16686102Diethyl aluminum chloride

Produkt 1

HCID 13349252HCID 13349252, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1004Phosphoric AcidKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

After 0.63 ml (0.63 mmol) of diethylaluminum chloride (hexane 1M solution) were added to a dried methylene chloride (3 ml) solution of 89.7 mg (0.24 mmol) of (S)-2-methanesulfonyloxy-3-octyl-3-undecanol (unrefined) at -78° C. under stirring, and stirred for two and a half hours at -78° C., the temperature was raised to 0° C. over an hour and a half. The reaction was stopped with three drops of phosphoric acid buffer solution (pH 7). The resultant suspension was diluted with ethyl acetate, dried with anhydrous sodium sulfate, filtered and concentrated. The oily residue was separated and refined by the use of silica gel column chromatography (hexane/ethyl acetate=35/1) to obtain (S)-10-methyl-9-octadecanone as a colorless oily substance (60.5 mg, yield 90%).

Aufarbeitung

  1. stirringstirred for two and a half hours at -78° C.
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oily residue was separated

Quellen und Nachweise

ORD-Eintrag
ord-524551429d3e4fc2bae4047df7efb279
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04604486

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