p-Toluenesulfonic acid → HCID 57225501, Verbindung

HRID 1067110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067110
O[C@:2]1([C:9]2[O:10][C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=C(C3C=CC=CC=3)[N:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[OH:8].COC(OC)(OC)C.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37](S(O)(=O)=O)=[CH:36][CH:35]=1>C(Cl)Cl>[C:34]1([C:44]2[N:13]=[C:9]([C@:2]34[O:8][C@H:3]3[CH2:4][CH2:5][CH2:6][CH2:7]4)[O:10][C:11]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 15050Trimethyl orthoacetateHCID 57102465(1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane

Produkt 1

HCID 57225501HCID 57225501, VerbindungAusbeute 38.251,199 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (1R,2S)-1,2-dihydroxy-1-(4,5-diphenyl-oxazol-2-yl)cyclohexane (18 g) in CH2Cl2 (200 ml) were added orthoacetic acid trimethyl ester (9.7 ml) and p-toluenesulfonic acid (20 mg) at room temperature under N2. After being stirred for 30 minutes, the solvent was evaporated in vacuo. The residue was diluted with CH2Cl2 (200 ml) and acetylbromide (5.8 ml) was added to the solution at 0° C. under N2. After being stirred for 2 hours at room temperature, the solvent was evaporated in vacuo, the residue was diluted with MeOH (200 ml), and K2CO3 (12 g) was added to the solution at room temperature. The mixture was stirred for 2 hours at the same temperature and partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give (1R,2S)-1-(4,5-diphenyl-oxazol-2-yl)-1,2-epoxycyclohexane (14.1 g).

Aufarbeitung

  1. customthe solvent was evaporated in vacuo
  2. additionThe residue was diluted with CH2Cl2 (200 ml) and acetylbromide (5.8 ml)
  3. additionwas added to the solution at 0° C. under N2
  4. stirringAfter being stirred for 2 hours at room temperature
  5. customthe solvent was evaporated in vacuo
  6. additionthe residue was diluted with MeOH (200 ml), and K2CO3 (12 g)
  7. additionwas added to the solution at room temperature
  8. stirringThe mixture was stirred for 2 hours at the same temperature
  9. custompartitioned between ethyl acetate and water
  10. washThe organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine
  11. customThe dried solvent was evaporated in vacuo
  12. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-927f7c0a336c4ce994dc0bd46a5ec461
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06245790B1

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