Thionyl Chloride → 4-Chloro-2-butynyl 4-Cyano-3,4-diphenylbutyrate

HRID 27827

Reaktionsgleichung

Reaktionsgleichung von HRID 27827
S(Cl)([Cl:3])=O.[C:5]([CH:7]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]([O:12][CH2:13][C:14]#[C:15][CH2:16]O)=[O:11])#[N:6]>N1C=CC=CC=1.CCOCC.C(Cl)Cl>[C:5]([CH:7]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]([O:12][CH2:13][C:14]#[C:15][CH2:16][Cl:3])=[O:11])#[N:6]

Komponenten

6

Edukt 2

HCID 24386Thionyl ChlorideHCID 128348444-Hydroxy-2-butynyl 4-Cyano-3,4-diphenylbutyrate

Produkt 1

HCID 128348464-Chloro-2-butynyl 4-Cyano-3,4-diphenylbutyrateAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Thionyl chloride (3.56 g, 30.0 mmol) was added via syringe over a 5 min period to a stirred solution of 8.00 g (24.0 mmol) of 4-hydroxy-2-butynyl 4-cyano-3,4-diphenylbutyrate in 2.4 ml of pyridine at 0°. The reaction mixture was stirred at room temperature for 2 hours in a flask equipped with a Drierite tube. The mixture was diluted with 40 ml of ether and 100 ml of methylene chloride and was washed sequentially with 40 ml of hydrochloric acid, 40 ml of saturated aqueous sodium bicarbonate, three 40-ml portions of water and 40 ml of saturated aqueous sodium chloride. The organic phase was dried (MgSO4), filtered, stripped and purified by column chromatography on silica gel (hexanes/methylene chloride) to yield 2.11 g (25%) of the title compound. The infrared and nmr spectra are in accord with the assigned structure.

Aufarbeitung

  1. customequipped with a Drierite tube
  2. washwas washed sequentially with 40 ml of hydrochloric acid, 40 ml of saturated aqueous sodium bicarbonate, three 40-ml portions of water and 40 ml of saturated aqueous sodium chloride
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. custompurified by column chromatography on silica gel (hexanes/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-f1a4210cb3344226aa5e2ecbc2e095af
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04224052

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