Hydrochloric Acid → 1,2-Epoxy-2-(2,5-difluorophenyl)butan-3-ol

HRID 731021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731021
Cl[CH2:2][C:3]([C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])([OH:13])[CH:4]([O:6]C(=O)C(C)(C)C)[CH3:5].C[O-].[Na+].Cl>C1COCC1.CO>[O:13]1[C:3]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])([CH:4]([OH:6])[CH3:5])[CH2:2]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 231170421-Chloro-2-(2,5-difluorophenyl)-3-pivaloyloxybutan-2-ol

Produkt 1

HCID 230742631,2-Epoxy-2-(2,5-difluorophenyl)butan-3-olAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1.70 g (5.3 mmol) of 1-chloro-2-(2,5-difluorophenyl)-3-(pivaloyloxy)butan-2-ol ((2S,3R)/(2R,3R)=94/6) in 20 mL of THF was cooled to 0° C., and 3.5 g (17.8 mmol) of a 28% solution of NaOMe in methanol was added thereto. The reaction was performed for 5 hours, and 20 mL of 1 M hydrochloric acid was added to stop the reaction. Then, extraction was performed with ethylacetate (30 mL). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain 1.51 g of a crude product. The resulting product was purified by column on silica gel to obtain 0.838 g of the title compound (yield: 79%) ((2R,3R)/(2S,3R)=98/2 (the diastereomeric ratio was measured by HPLC under the same HPLC measurement conditions as those in Example 10, (2R,3R) 32 minutes, (2S,3R) 30 minutes). 1H-NMR (400 MHz, CDCl3) (2R,3R) δ: 1.70 (d, 3H, J=6.6 Hz), 2.80 (d, 1H, J=5.1 Hz), 3.34 (d, 1H, J=5.1 Hz), 4.17 (q, 1H, 6.6 Hz), 6.98-7.00 (m, 2H), 7.14-7.26 (m, 1H)

Aufarbeitung

  1. customthe reaction
  2. extractionThen, extraction
  3. dry with materialAfter drying over anhydrous sodium sulfate, concentration
  4. customto obtain 1.51 g of a crude product
  5. customThe resulting product was purified by column on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c3d04a554bf74fc4b58f8453741186c0
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582781B2

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