Toluene → 2-(2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(dimethyl(2-methyl-2-propyl)silyloxy)propyl)phenyl)-2-propoxy)tetrahydropyran

HRID 342013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342013
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([O:33][Si:34]([CH3:40])([CH3:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([OH:32])([CH3:31])[CH3:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[O:41]1[CH:46]=[CH:45][CH2:44][CH2:43][CH2:42]1.[Br-].C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([O:33][Si:34]([CH3:40])([CH3:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([O:32][CH:42]4[CH2:43][CH2:44][CH2:45][CH2:46][O:41]4)([CH3:31])[CH3:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 80803,4-dihydro-2H-pyran2×HCID 517696Phosphine, triphenyl-, hydrobromide2×HCID 536347942-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(dimethyl(2-methyl-2-propyl)silyloxy)propyl)phenyl)-2-propanol

Produkt 1

HCID 539396992-(2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(dimethyl(2-methyl-2-propyl)silyloxy)propyl)phenyl)-2-propoxy)tetrahydropyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 0.2M solution of the tertiary alcohol of Step 4 in CH2Cl2 were added 5 equiv. of dihydropyran and 0.1 equiv. of triphenylphosphonium bromide and the mixture was stirred at reflux for 1 day. Then, the same amount of dihydropyran and triphenylphosphonium bromide were added and the mixture stirred at reflux another day. Toluene was added and the resulting solution was filtered through silica with EtOAc:toluene 0:100 to 2:98 to afford the title product.

Aufarbeitung

  1. temperatureat reflux for 1 day
  2. stirringthe mixture stirred
  3. temperatureat reflux another day
  4. filtrationthe resulting solution was filtered through silica with EtOAc:toluene 0:100 to 2:98

Quellen und Nachweise

ORD-Eintrag
ord-8d250cb1a2c547de9e97ae7b9dfbf062
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856322

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