Hydrochloric Acid → (4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile

HRID 973517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 973517
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Li]CCCC.[O:23]1[C@H:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24]1.Cl>O1CCCC1.CCCCCC.CN(P(N(C)C)(N(C)C)=O)C>[OH:23][C@H:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:10][CH:11]=1)[C:16]#[N:17]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 1620686(2R)-2-HexyloxiraneHCID 15733995(4'-Methoxy[1,1'-biphenyl]-4-yl)acetonitrileHCID 178418339Butyllithium

Produkt 1

HCID 54327812(4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrileAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

To a solution of 1.02 g (4.6 mmol) of 4-(4-methoxyphenyl)phenylacetonitrile in 40 ml of tetrahydrofuran (THF) was added, at -78° C., 1.5 M n-BuLi solution in hexane in an amount of 3.6 ml (5.5 mmol). This mixture was stirred for 1 hour. Thereto were added a solution of 705 mg (5.5 mmol) of (R)-1,2-epoxyoctane in 20 ml of THF and 5 ml of HMPA. The resulting mixture was warmed to room temperature, and then stirred overnight. The reaction mixture was neutralized with 3 M hydrochloric acid, and then subjected to extraction with 300 ml of ethyl acetate. The resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, filtered, and then concentrated. The residue was separated and purified by column chromatography (hexane/ethyl acetate=3/1), thereby obtaining 1.05 g (yield 65%) of (4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile.

Aufarbeitung

  1. stirringstirred overnight
  2. extractionsubjected to extraction with 300 ml of ethyl acetate
  3. washThe resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was separated
  8. custompurified by column chromatography (hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-e54df340496945618826c3278ce6295b
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05064564

Notizen zur Reaktion

Wird geladen…