Tetrahydrofuran → 2-(3,4-Dichloro-phenyl)-5-(tetrahydro-pyran-4-yloxy)-pentanenitrile

HRID 1637182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637182
[H-].[Na+].[C:3]1([CH2:9][C:10]#N)[CH:8]=[CH:7]C=CC=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21]#[N:22])[CH:16]=[CH:17][C:18]=1[Cl:19].Br[CH2:24][CH2:25][CH2:26][OH:27].C1C[O:31]CC1>C(=O)=O.CC(C)=O>[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]([CH2:24][CH2:25][CH2:26][O:27][CH:3]2[CH2:8][CH2:7][O:31][CH2:10][CH2:9]2)[C:21]#[N:22])[CH:16]=[CH:17][C:18]=1[Cl:19]

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran3×HCID 123083-Bromo-1-propanolHCID 24758Sodium hydrideHCID 193480233,4-Dichloro-phenylacetonitrile phenylacetonitrile

Produkt 1

HCID 158876512-(3,4-Dichloro-phenyl)-5-(tetrahydro-pyran-4-yloxy)-pentanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18522661Acetone cardiceLösungsmittel

Versuchsvorschrift

To a suspension of NaH (7.6 g, 0.191 mol) in THF (90 mL) was added slowly a solution of 3,4-dichloro-phenylacetonitrile phenylacetonitrile (32.3 g, 0.174 mol) in dry THF (40 mL). The mixture was stirred at room temperature for 2 hours, then cooled in dry ice-acetone bath. A solution of THP protected 3-bromopropanol (42.6 g, 0.191 mol, 1.1 eq) in dry THF (50 mL) was added dropwise to this solution. After the addition was completed, the reaction was warmed to room temperature and stirred at room temperature overnight (20 hours). The reaction was then quenched with saturated NH4Cl solution (ca. 5 mL) and ether (300 mL) was added. The organic phase was then washed with saturated NaHCO3, brine, and dried (MgSO4). After filtration, solvent was removed, and the crude oil was purified by flash column chromatography (Hexane-AceOEt/8:1). The product weight 46.8 g (82.2%) as light yellow oil.

Aufarbeitung

  1. additionwas added dropwise to this solution
  2. additionAfter the addition
  3. temperaturethe reaction was warmed to room temperature
  4. stirringstirred at room temperature overnight (20 hours)
  5. customThe reaction was then quenched with saturated NH4Cl solution (ca. 5 mL) and ether (300 mL)
  6. additionwas added
  7. washThe organic phase was then washed with saturated NaHCO3, brine
  8. dry with materialdried (MgSO4)
  9. filtrationAfter filtration, solvent
  10. customwas removed
  11. customthe crude oil was purified by flash column chromatography (Hexane-AceOEt/8:1)

Quellen und Nachweise

ORD-Eintrag
ord-6ad562d1ca86466cba7e1b05983a69be
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040316

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