Water → 1-[2-Hydroxy-4-(4-iodo-benzyloxy)-3-propyl-phenyl]-ethanone

HRID 1818551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818551
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][CH:4]=1.[OH:10][C:11]1[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]([OH:20])[CH:14]=[CH:13][C:12]=1[C:21](=[O:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(C)=O>[OH:10][C:11]1[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]([O:20][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([I:9])=[CH:5][CH:4]=2)[CH:14]=[CH:13][C:12]=1[C:21](=[O:23])[CH3:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 9542584-Iodobenzyl bromideHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Produkt 1

HCID 574383871-[2-Hydroxy-4-(4-iodo-benzyloxy)-3-propyl-phenyl]-ethanoneAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Add 1-bromomethyl-4-iodo-benzene (10.00 g, 33.7 mmol) to a solution of 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (6.54 g, 33.7 mmol) and cesium carbonate (13.2 g, 40.4 mmol) in acetone (500 mL) and stir. After 48 hours, pour the reaction into water and extract with ethyl acetate. Combine the organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography eluting with a gradient of ethyl acetate:hexanes to yield the title product as a yellow solid (7.20 g, 52%): 1H NMR (CDCl3) δ 0.95 (t, 3H), 1.56 (sextet, 2H), 2.56 (s, 3H), 2.69 (t, 2H), 5.09 (s, 2H), 6.43 (d, 1H), 7.15 (d, 2H), 7.57 (d, 1H), 7.73 (d, 2H), 12.74 (s, 1H).

Aufarbeitung

  1. additionpour
  2. extractionextract with ethyl acetate
  3. dry with materialdry with sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto give a residue
  7. customPurify the residue by flash chromatography
  8. washeluting with a gradient of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3d163fdf169c459f8d6a3280e5169ec6
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598423B2

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