Ethyl Acetate → ethyl (R)-{3-{[2-(4,5-diphenyloxazole-2-yl)-1-hydroxy-2-cyclohexen-1-yl]methyl}phenoxy}-acetate

HRID 379319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379319
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@:19]([O:49][Si](C)(C)C)([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([O:31][Si](C(C)(C)C)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:26]=4)[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:72][CH2:73][O:74][C:75]([CH3:77])=[O:76]>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@@:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=4)[O:31][CH2:77][C:75]([O:74][CH2:73][CH3:72])=[O:76])([OH:49])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 15550206(R)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyloxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]-2-cyclohexene

Produkt 1

HCID 15550207ethyl (R)-{3-{[2-(4,5-diphenyloxazole-2-yl)-1-hydroxy-2-cyclohexen-1-yl]methyl}phenoxy}-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyloxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]-2-cyclohexene (10 g) in THF (50 ml) was added tetrabutylammonium fluoride (41 ml, 1M solution in THF) at room temperature. After being stirred for 4 hours, the mixture was diluted with EtOAc. The mixture was washed with 1N-HCl solution and brine and evaporated. The residue was dissolved in DMF (50 ml), followed by addition of K2CO3 (5 g) and ethyl bromoacetate (2.0 ml) at room temperature. The mixture was stirred for 2 hours at the same temperature and partitioned between EtOAc and water. The organic layer was washed with water and brine and evaporated in vacuo. The residue was purified by chromatography on silica gel to give ethyl (R)-{3-{[2-(4,5-diphenyloxazole-2-yl)-1-hydroxy-2-cyclohexen-1-yl]methyl}phenoxy}-acetate (5.3 g).

Aufarbeitung

  1. washThe mixture was washed with 1N-HCl solution and brine
  2. customevaporated
  3. dissolutionThe residue was dissolved in DMF (50 ml)
  4. additionfollowed by addition of K2CO3 (5 g) and ethyl bromoacetate (2.0 ml) at room temperature
  5. stirringThe mixture was stirred for 2 hours at the same temperature
  6. custompartitioned between EtOAc and water
  7. washThe organic layer was washed with water and brine
  8. customevaporated in vacuo
  9. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-bf2eb6408ae7429d83bed8b74b6077d7
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297267B1

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