3-(2-(4-((3,4-Dichlorobenzyl)oxy)phenyl)-2-oxoethoxy)-4-fluorobenzonitrile → 3-{(S)-2-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2-hydroxy-ethoxy}-4-fluoro-benzonitrile

HRID 879677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879677
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:25])[CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=2[F:24])[C:19]#[N:20])=[CH:9][CH:8]=1>C1(C)C=CC=CC=1.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]([OH:25])[CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=2[F:24])[C:19]#[N:20])=[CH:9][CH:8]=1

Komponenten

4

Edukt 1

HCID 583271623-(2-(4-((3,4-Dichlorobenzyl)oxy)phenyl)-2-oxoethoxy)-4-fluorobenzonitrile

Produkt 1

HCID 583274143-{(S)-2-[4-(3,4-Dichloro-benzyloxy)-phenyl]-2-hydroxy-ethoxy}-4-fluoro-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

400 mL dry THF, 93 mL of 1M (S)-CBS reagent in toluene, and 30.3 g borane-diethylaniline complex were stirred together 10 min at rt. 3-{2-[4-(3,4-dichloro-benzyloxy)-phenyl]-2-oxo-ethoxy}-4-fluoro-benzonitrile (40 g) in 1.2 L dry THF was then added through an addition funnel at rt over 10 min. The mixture stirred for 15 min, then was quenched by slow addition of 100 mL MeOH. After gas evolution ceased the mixture was evaporated to a yellow oil. The oil was dissolved in 200 mL diethyl ether, precipitated with 1.2 L of hexanes and stored 18 h at −20° C. The desired product was collected by filtration and dried under vacuum to give 28.9 g. 1H NMR (400 MHz, CDCl3): 7.54 (d, 1H), 7.46 (d, 1H), 7.38 (m, 2H), 7.3-7.15 (m, 4H), 6.97 (m, 2H), 5.13 (m, 1H), 5.03 (s, 2H), 4.10 (m, 2H), 2.63 (d, 1H).

Aufarbeitung

  1. customwas quenched by slow addition of 100 mL MeOH
  2. customwas evaporated to a yellow oil
  3. dissolutionThe oil was dissolved in 200 mL diethyl ether
  4. customprecipitated with 1.2 L of hexanes
  5. waitstored 18 h at −20° C
  6. filtrationThe desired product was collected by filtration
  7. customdried under vacuum
  8. customto give 28.9 g

Quellen und Nachweise

ORD-Eintrag
ord-8dfa78e32bbe427ba964cc9e84e65444
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987295B2

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