Tetrahydrofuran → 4-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrile

HRID 1743724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743724
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:26]=[CH:25][C:11]([O:12][CH:13]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[CH2:14][CH:15]=[CH2:16])=[CH:10][CH:9]=1.B.CSC.C1C[O:34]CC1>CCOCC>[OH:34][CH2:16][CH2:15][CH2:14][CH:13]([C:17]1[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=1)[O:12][C:11]1[CH:25]=[CH:26][C:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 12423031(Dimethyl sulfide)trihydroboronHCID 222356714-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile

Produkt 1

HCID 222354084-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

4-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile (4.6 g, 13 mmol; from step (d) above) was dissolved in dry THF (50 mL) under argon and cooled to −5° C. Borane-methylsulfide complex (BH3×SMe2) (3.5 mL of a 2 M solution in ether) was added dropwise at 0 to 5° C. The mixture was stirred at that temperature for 1.5 h. After 4 h at rt, tlc showed that the reaction was complete. The reaction mixture was quenched with 14 mL of H2O and 5 g of NaBO3. The mixture was stirred overnight, the solvent decanted off, and the residue treated with ether and decanted. The combined organic fractions were washed with brine, dried (Na2SO4), and evaporated. The crude product was purified by chromatography on silica (iso-propanol:ethyl acetate:heptane; 5:20:70). Yield: 2.44 g (58%).

Aufarbeitung

  1. waitAfter 4 h at rt
  2. customThe reaction mixture was quenched with 14 mL of H2O and 5 g of NaBO3
  3. stirringThe mixture was stirred overnight
  4. customthe solvent decanted off
  5. additionthe residue treated with ether
  6. customdecanted
  7. washThe combined organic fractions were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customThe crude product was purified by chromatography on silica (iso-propanol:ethyl acetate:heptane; 5:20:70)

Quellen und Nachweise

ORD-Eintrag
ord-7262b0c1886c46889a4317a2821e3766
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012074B2

Notizen zur Reaktion

Wird geladen…