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 865480ノート

反応式

HRID 865480 の反応式
[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

参加物

6

反応物 4

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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f48c6bca47654749bafc144593613d76
出典データセット
uspto-grants-1996_10
特許番号
US05565473

反応ノート

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