(4-Fluorobenzyl)triphenylphosphonium chloride → 4-(4-(4-Fluorobenzylidene)-1-piperidinyl)benzonitrile

HRID 731543

Reaktionsgleichung

Reaktionsgleichung von HRID 731543
[Cl-].[F:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[Li]CCCC.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][C:45](=O)[CH2:44][CH2:43]2)=[CH:38][CH:37]=1)#[N:35]>C1COCC1>[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[C:45]2[CH2:46][CH2:47][N:42]([C:39]3[CH:40]=[CH:41][C:36]([C:34]#[N:35])=[CH:37][CH:38]=3)[CH2:43][CH2:44]2)=[CH:27][CH:28]=1

Komponenten

5

Edukt 3

HCID 2733554(4-Fluorobenzyl)triphenylphosphonium chlorideHCID 110198874-(4-Oxopiperidin-1-yl)benzonitrileHCID 178418339Butyllithium

Produkt 1

HCID 591866134-(4-(4-Fluorobenzylidene)-1-piperidinyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of the 4-fluorobenzyl triphenylphosphonium chloride (0.737 g, 1.81 mmol) in THF (10 mL) was treated with nBuLi (724 μL of a 1.6M solution in hexanes, 1.81 mmol) at 0° C., treated with 1-(4′-cyanophenyl)-4-oxopiperidine (prepared according to the procedure described in Synthesis 1981, 606-608, 0.300 g, 1.51 mmol), and gradually warmed to room temperature overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl and the aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography eluting with 10% ethyl acetate in hexanes to give the desired product. (0.268 g, 61%). MS (ESI) m/e 292 (M+H)+.

Aufarbeitung

  1. customprepared
  2. customdescribed in Synthesis 1981, 606-608, 0.300 g, 1.51 mmol), and
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel chromatography
  9. washeluting with 10% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7b558142890d4dbbb5ea4e86413657e8
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585858B2

Verknüpfte Notizen

Wird geladen…