Prenderol → 5-(5,5-Diethyl-1,3-dioxan-2-yl)-2-fluorobenzenecarbonitrile

HRID 250529

Reaktionsgleichung

Reaktionsgleichung von HRID 250529
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:12]([C:14]([CH2:19][CH3:20])([CH2:17]O)[CH2:15][OH:16])[CH3:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:12]([C:14]1([CH2:19][CH3:20])[CH2:15][O:16][CH:10]([C:7]2[CH:8]=[CH:9][C:2]([F:1])=[C:3]([C:4]#[N:5])[CH:6]=2)[O:11][CH2:17]1)[CH3:13]

Komponenten

5

Edukt 3

HCID 8284PrenderolHCID 521998p-Toluenesulfonic acid monohydrateHCID 27695822-Fluoro-5-formylbenzonitrile

Produkt 1

HCID 113913915-(5,5-Diethyl-1,3-dioxan-2-yl)-2-fluorobenzenecarbonitrileAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-Fluoro-5-formylbenzonitrile (250 mg, 1.68 mmol), 2,2-diethyl-1,3-propanediol (776 mg, 5.87 mmol) and a catalytic amount of p-toluenesulfonic acid monohydrate were refluxed in toluene (25 mL) overnight in a Dean-Stark apparatus. The reaction mixture was then concentrated and the residue dissolved in chloroform (50 mL) and washed with saturated sodium bicarbonate solution (2×25 mL) then brine (1×25 mL). The organic phase was dried (Na2SO4) and evaporated to give an oil. The oil was then chromatographed on silica gel (4:1 hexane/ethyl acetate) to give 5-(5,5-diethyl-1,3-dioxan-2-yl)-2-fluorobenzenecarbonitrile (43) as a light yellow oil (401 mg, 91%). 1H NMR (MeOD, 300 MHz): δ 0.90, t (7.7 Hz), CH2CH3; 0.97, t (7.5 Hz), CH2CH3; 1.25, q (7.6 Hz), CH2CH3; 1.86, q (7.6 Hz), CH2CH3; 3.72, d (11.5 Hz), CH2O; 4.02, d (11.4 Hz), CH2O; 5.52, s, H2; 7.42, t (9.3 Hz), H3; 7.86, m, H4,6. ESI (+ve) MS: m/z 264 (M+H, 11%).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue dissolved in chloroform (50 mL)
  3. washwashed with saturated sodium bicarbonate solution (2×25 mL)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customto give an oil
  7. customThe oil was then chromatographed on silica gel (4:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b990f2a751794db3870e44c7a9595ef4
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863313B2

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