(Diethylamino)sulfur trifluoride → 2-(1-Fluoro-5-phenylpentyl)-2-oxiranecarboxylic acid methyl ester

HRID 2232655

Reaktionsgleichung

Reaktionsgleichung von HRID 2232655
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][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][O:15]1)=[O:13]

Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 143489022-(5-Phenyl-1-hydroxypentyl)-2-oxiranecarboxylic acid methyl ester

Produkt 1

HCID 143489052-(1-Fluoro-5-phenylpentyl)-2-oxiranecarboxylic acid methyl esterAusbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2.44 g (15 mmol; 2.0 ml) of diethylaminosulfur trifluoride in 50 ml of methylene chloride cooled to -78° C. under a nitrogen atmosphere is added dropwise a solution of 2.00 g (7.6 mmol) of 2-[1-hydroxy-5-phenylpentyl]-2-oxiranecarboxylic acid methyl ester (isomer A) in 50 ml of methylene chloride over 30 minutes. The mixture is stirred at -78° C. for 90 minutes and then is allowed to come to room temperature. The mixture is stirred at room temperature for 1.5 hours, is quenched with a saturated aqueous solution of sodium bicarbonate and is extracted with ethyl ether. The combined ethereal extracts are dried over magnesium sulfate, filtered and rotoevaporated. The resulting oil is purified chromatographically (silica gel; hexane:ethyl acetate (9:1)) to give 1.19 g of the title compound (Rf 0.54 in hexane:ethyl ether (3:2)): IR (neat) γ 1750 cm-1 ; NMR (CDCl3) δ 1.40-1.96 (6H, m), 2.64 (2H, t, J=8 Hz), 3.07 (1H, dd, J=4, 6 Hz), 3.15 (1H, d, J=6 Hz), 3.15 (1H, d, J=6 Hz), 3.79 (3H, s), 5.14 (1H, ddd, JHF =48 Hz, J=10, 3 Hz), 7.21 (2H, d, J=8 Hz) and 7.31 (2H, d, J=8 Hz).

Aufarbeitung

  1. customto come to room temperature
  2. stirringThe mixture is stirred at room temperature for 1.5 hours
  3. customis quenched with a saturated aqueous solution of sodium bicarbonate
  4. extractionis extracted with ethyl ether
  5. dry with materialThe combined ethereal extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe resulting oil is purified chromatographically (silica gel; hexane:ethyl acetate (9:1))

Quellen und Nachweise

ORD-Eintrag
ord-e8cb0699909c4e7da290e5f59a089625
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04788306

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