Tetrahydrofuran → Tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate

HRID 846189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846189
[Cl-].C([Al+][CH2:5][CH3:6])C.Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH2:16]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH:34](SC1N(CCCC(O)=O)N=NN=1)C(O)=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[O:50]1CCCC1>CCCCCC.[Zn].[Cu]Br>[OH:50][CH:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:6][CH:5]=1)[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Komponenten

8

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 79177tert-Butyl bromoacetateHCID 16686102Diethyl aluminum chlorideHCID 198803822-(2-Dodecylphenyl)-2-[[1-(3-carboxypropyl)-5-tetrazolyl]thio]acetic acid

Produkt 1

HCID 15617420Tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 24593copper(I) bromideKatalysatorHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A solution of diethlaluminum chloride (0.0082 moles, 8.2 ml) in hexane was added to a slurry of zinc dust (0.0111 mol: 0.7248 g) and a catalytic amount of copper (I) bromide (0.004 mol; 0.0585 g) in anhydrous tetrahydrofuran (40 ml) while stirring under argon at 20° C. the resulting mixture was then cooled to -20° C. in an ice-methanol bath. A solution of t-butyl bromoacetate (0.0082 mol; 1.32 ml) and 2-(8-phenyloctyl)benzylaldehyde of Example 5(a) or (b) (0.0082 moles; 2.3969 g) in anhydrous tetrahydrofuran was added slowly over 60 min. The reaction was stirred overnight and was permitted to warm up slowly to room temperature. The mixture was filtered to remove zinc, concentrated, and azeotroped with methylene chloride. The resulting oil was then chromatographed on silica using 5% ethyl acetate in hexane with 0.5% formic acid to yield the desired product.

Aufarbeitung

  1. temperatureto warm up slowly to room temperature
  2. filtrationThe mixture was filtered
  3. customto remove zinc
  4. concentrationconcentrated
  5. customazeotroped with methylene chloride
  6. customThe resulting oil was then chromatographed on silica using 5% ethyl acetate in hexane with 0.5% formic acid

Quellen und Nachweise

ORD-Eintrag
ord-6f16b235f1344b378bd1cdc68173c15c
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05135938

Notizen zur Reaktion

Wird geladen…