Ethyl ketone → 5-Fluoro-3-(3-hydroxypent-3-yl)[O-(3,4-dimethoxybenzyl)]phenol

HRID 741797

Reaktionsgleichung

Reaktionsgleichung von HRID 741797
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH:3]=1.[Li]CCCC.[CH3:26][CH2:27][C:28](=[O:31])[CH2:29][CH3:30]>C1COCC1>[F:8][C:6]1[CH:7]=[C:2]([C:28]([OH:31])([CH2:29][CH3:30])[CH2:27][CH3:26])[CH:3]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH:5]=1

Komponenten

5

Edukt 3

HCID 7288Ethyl ketoneHCID 194269851-Bromo-3-(3,4-dimethoxybenzyloxy)-5-fluorobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 701948305-Fluoro-3-(3-hydroxypent-3-yl)[O-(3,4-dimethoxybenzyl)]phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-bromo-3-(3,4-dimethoxybenzyloxy)-5-fluorobenzene (Step 1) (1.02 g) in THF (10 mL) at -78° C. was added n-BuLi (1.5 mL of a 2.2M solution) dropwise. After 30 min. 3-pentanone (0.33 mL) was added and after 30 min. the bath was removed and the mixture stirred for 10 min. The reaction mixture was quenched with NH4OAc buffer and extracted with EtOAc. The organics were dried (MgSO4) and concentrated. Chromatography of the residue (silica gel; hexane/EtOAc (3:1) provided the title compound as a colorless oil.

Aufarbeitung

  1. customwas removed
  2. customThe reaction mixture was quenched with NH4OAc buffer
  3. extractionextracted with EtOAc
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-562b24e210d54286a4ce0bb08e495993
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552437

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