Sodium Hydroxide → (R)-2-(4-chloro-3-fluorophenyl)oxirane

HRID 530588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530588
CC1C=CC(S(O[CH2:12][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([F:22])[CH:16]=2)[OH:14])(=O)=O)=CC=1.FC1C=CC(C(=O)C)=CC=1C(F)(F)F.[OH-].[Na+]>CCOCC>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@@H:13]2[CH2:12][O:14]2)=[CH:16][C:17]=1[F:22]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 6056784'-Fluoro-3'-(trifluoromethyl)acetophenoneHCID 117870261(R)-2-(4-chloro-3-fluorophenyl)-2-hydroxyethyl 4-methylbenzenesulfonate

Produkt 1

HCID 94590788(R)-2-(4-chloro-3-fluorophenyl)oxirane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

(R)-2-(4-chloro-3-fluorophenyl)-2-hydroxyethyl 4-methylbenzenesulfonate (prepared as previously described in Example 1 (steps a-b) except substituting 1-(3-chloro-4-fluorophenyl)ethanone for 1-(4-fluoro-3-(trifluoromethyl)phenyl)ethanone, 3.35 g, 9.72 mmol) was dissolved in ether (80 mL) and 2N NaOH solution (25 mL) was added. The mixture was stirred at room temperature for 6 h until all starting material was consumed. The mixture was separated and the ether layer was washed with water. The organic layer was dried with sodium sulfate and solvents were removed to afford (R)-2-(4-chloro-3-fluorophenyl)oxirane as a colorless oil which was dried in vacuum (1.66 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.71-2.80 (m, 1H) 3.18 (dd, J=5.31, 4.04 Hz, 1H) 3.82-3.89 (m, 1H) 7.01-7.12 (m, 2H) 7.39 (dd, J=8.46, 7.45 Hz, 1H).

Aufarbeitung

  1. customwas consumed
  2. customThe mixture was separated
  3. washthe ether layer was washed with water
  4. dry with materialThe organic layer was dried with sodium sulfate and solvents
  5. customwere removed

Quellen und Nachweise

ORD-Eintrag
ord-226c60bdf29f44469e0c0d048a6b01b2
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353096B2

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