(Diethylamino)sulfur trifluoride → HCID 54007397, Verbindung

HRID 2232624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2232624
C(N(S(F)(F)[F:7])CC)C.[CH3:10][O:11][C:12]([C:14]1([CH:17](O)[CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:16][O:15]1)=[O:13]>C(Cl)Cl>[CH3:10][O:11][C:12]([C:14]1([CH:17]([F:7])[CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH2:16][O:15]1)=[O:13]

Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 53948093HCID 53948093, Verbindung

Produkt 1

HCID 54007397HCID 54007397, VerbindungAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 967 mg (6 mmol, 733 μl) of diethylaminosulfur trifluoride in 25 ml of methylene chloride cooled to -78° C. under a nitrogen atmosphere is added dropwise a solution of 945 mg (3 mmol) of 2-[5-(4-chlorophenoxy)-1-hydroxypentyl]-2-oxiranecarboxylic acid methyl ester (isomer A) in 25 ml of methylene chloride over 30 minutes. The mixture is stirred at -78° C. for 30 minutes and then is allowed to come to room temperature. The mixture is stirred at room temperature for 1.5 hours, is quenched with brine and is extracted with ethyl ether. The combined ethereal extracts are dried over magnesium sulfate, filtered and rotoevaporated to give a crude solid. Trituration with cyclohexane:isopropyl ether and subsequent high vacuum drying affords 597 mg of the title compound (isomer A) (Rf 0.45 in hexane:ethyl ether (1:1)): m.p. 76°-78° C.; IR (KBr) γ1740, 1497, 1257, 832 and 758 cm-1 ; NMR (CDCl3) δ1.54-2.02 (6H, m), 3.10 (1H, dd, J=3, 6 Hz), 3.18 (1H, d, J=6 Hz), 3.80 (3H, s), 3.96 (2H, t, J=7 Hz), 5.19 (1H, ddd, JHF = 48 Hz, 10, 3 Hz), 6.85 (2H, d, J=7 Hz) and 7.27 (2H, d, J=7 Hz).

Aufarbeitung

  1. customto come to room temperature
  2. stirringThe mixture is stirred at room temperature for 1.5 hours
  3. customis quenched with brine
  4. extractionis extracted with ethyl ether
  5. dry with materialThe combined ethereal extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. customto give a crude solid
  8. dry with materialTrituration with cyclohexane:isopropyl ether and subsequent high vacuum drying

Quellen und Nachweise

ORD-Eintrag
ord-15f340b62f964349adf4e7d03c2b07ea
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04788304

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