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Diisopropylamine → Ethyl 3-hydroxy-3-(1-trityl-1h-imidazol-4-yl)propanoate

HRID 724205
ノート
印刷プレビュー

反応式

HRID 724205 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([N:32]1[CH:36]=[C:35]([CH:37]=[O:38])[N:34]=[CH:33]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+].[C:41]([O:44][CH2:45][CH3:46])(=[O:43])[CH3:42]>C1COCC1.CCCCCC.O>[OH:38][CH:37]([C:35]1[N:34]=[CH:33][N:32]([C:13]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:36]=1)[CH2:42][C:41]([O:44][CH2:45][CH3:46])=[O:43]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 178418339Butyllithium

生成物 1

HCID 21879633Ethyl 3-hydroxy-3-(1-trityl-1h-imidazol-4-yl)propanoate

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒3 回
HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

Diisopropylamine (33.8 ml) was dissolved in dry THF (445 ml) under an argon atmosphere. A solution (1.6 M; 150 ml) of n-butyl lithium in hexane was added at not more than 0° C. with stirring under ice-cooling (ice-salt), and the mixture was stirred for 30 min. The mixture was then cooled to −70° C. in a dry ice-acetone bath and ethyl acetate (23.5 ml)/dry THF (60 ml) solution was added at not more than −65° C. The mixture was stood with stirring for 1 h 20 min. The reaction mixture was added to a solution (1185 ml) cooled to −70° C. of 1-trityl-4-formyl-1H-imidazole (67.7 g) in dry THF at not more than −60° C., and the mixture was stirred for 1 h. A 20% aqueous ammonium chloride solution (445 ml) was added to stop the reaction and the mixture was allowed to warm to room temperature over 1 h. An equivalent amount of water was added and the mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layer was combined and the mixture was dried over anhydrous sodium sulfate. The solvent was evaporated, and the precipitated crystals were finely divided with hexane, collected by filtration and dried to give the title compound (77.26 g) as colorless crystals.

後処理

  1. stirringthe mixture was stirred for 30 min
  2. stirringwith stirring for 1 h 20 min
  3. stirringthe mixture was stirred for 1 h
  4. customthe reaction
  5. temperatureto warm to room temperature over 1 h
  6. customthe mixture was partitioned
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. dry with materialthe mixture was dried over anhydrous sodium sulfate
  9. customThe solvent was evaporated
  10. filtrationcollected by filtration
  11. customdried

出典と根拠

ORDレコード
ord-e8f2cfee87f549c2adf8dd519bd6cbd0
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07141598B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート