2-Cyclohexen-1-one, 4,4-diphenyl- → (3aRS,7aRS)-7,7-diphenyl-2-(phenylacetyl)-4-perhydroisoindolone

HRID 1029954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029954
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([CH2:24][N:25]1CN(C[Si](C)(C)C)CN(C[Si](C)(C)C)[CH2:26]1)(C)C.[C:41]1([CH2:47][C:48](F)=[O:49])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>ClC(Cl)CCl.ClCCl>[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]3[CH:11]([CH2:24][N:25]([C:48](=[O:49])[CH2:47][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH2:26]3)[C:10](=[O:13])[CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 1382802-Cyclohexen-1-one, 4,4-diphenyl-HCID 642641Phenylacetyl fluorideHCID 135150051,3,5-Tris-trimethylsilylmethyl-1,3,5-triazine

Produkt 1

HCID 67916161(3aRS,7aRS)-7,7-diphenyl-2-(phenylacetyl)-4-perhydroisoindoloneAusbeute 12,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 65741,1,2-TrichloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A solution of 4,4-diphenylcyclohex-2-en-1-one (25 g) and 1,3,5-tris-trimethylsilylmethyl-1,3,5-triazine (1.65 g) in 1,1,2-trichloroethane (17 cc) is treated with a solution of phenylacetyl fluoride (1.8 g) in 1,1,2-trichloroethane (5 cc) and the mixture is then heated at 120° C. for 22 hours. The reaction mixture is diluted with dichloromethane (100 cc), washed with saturated sodium bicarbonate solution (100 cc) and with saturated sodium chloride solution (100 cc), dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 3 cm, height 27 cm), eluting with a mixture of cyclohexane and ethyl acetate (90/10 by volume) and collecting 35 cc fractions. Fractions 33 to 36 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aRS,7aRS)-7,7-diphenyl-2-(phenylacetyl)-4-perhydroisoindolone (0.25 g) in the form of white crystals melting at 212° C.

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate solution (100 cc) and with saturated sodium chloride solution (100 cc)
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 3 cm, height 27 cm)
  5. washeluting with a mixture of cyclohexane and ethyl acetate (90/10 by volume)
  6. customcollecting 35 cc fractions
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-51de26bf460e4db3aec4753e5dc9aa13
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102667

Notizen zur Reaktion

Wird geladen…