Toluene → HCID 22285063、化合物

HRID 1061880

反応式

HRID 1061880 の反応式
C1(C)C=CC=CC=1.C([Li])CCC.Br[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]([N:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[O:25])[CH:18]=[CH:17]2.[CH3:33][CH:34]([CH3:61])[C:35]([C:37]1[N:38]=[CH:39][N:40]([C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=1)=[O:36]>CCCCCC.C1COCC1.O>[OH:36][C:35]([C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]([N:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[O:25])[CH:18]=[CH:17]2)([C:37]1[N:38]=[CH:39][N:40]([C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=1)[CH:34]([CH3:61])[CH3:33]

参加物

8

反応物 4

HCID 1140TolueneHCID 10150490isopropyl(1-trityl-1H-imidazol-4-yl)ketoneHCID 218796396-bromo-N,N-diisopropyl-2-naphthamideHCID 178418339Butyllithium

生成物 1

HCID 22285063HCID 22285063、化合物収率 89.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

To a solution of toluene (1000 mL) containing a solution (1.6 M : 98.3 mL) of butyllithium in hexane was dropwise added a solution (250 mL) of 6-bromo-N,N-diisopropyl-2-naphthamide (50.0 g) in THF at −70° C. The mixture was stirred at the same temperature for 30 min., and a solution (200 mL) of 2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanone (47.5 g) in THF was added dropwise. The mixture was stirred for 20 min. Water was added and the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the residue was recrystallized from isopropyl ether to give the title compound (71.1 g) as a colorless powder.

後処理

  1. stirringThe mixture was stirred for 20 min
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was recrystallized from isopropyl ether

出典と根拠

ORDレコード
ord-c6d69dfcdc694d08b1f0d374062b7e15
出典データセット
uspto-grants-2005_11
特許番号
US06960586B2

関連ノート

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