Hydrochloric Acid → alpha-Ethyl-1-(triphenylmethyl)-1H-imidazole-4-methanol

HRID 1924259ノート

反応式

HRID 1924259 の反応式
[CH2:1](I)[CH3:2].[Li]C(C)(C)C.CCCCC.[C:14]([N:33]1[CH:37]=[C:36]([CH:38]=[O:39])[N:35]=[CH:34]1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>CCOCC.C1COCC1>[C:14]([N:33]1[CH:37]=[C:36]([CH:38]([OH:39])[CH2:1][CH3:2])[N:35]=[CH:34]1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 8003PentaneHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 178418306HCID 178418306、化合物

生成物 1

HCID 12344795alpha-Ethyl-1-(triphenylmethyl)-1H-imidazole-4-methanol収率 56%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a 100 ml, three-necked flask fitted with a magnetic stirrer, under inert atmosphere, ethyl iodide (1.1 ml, 0.0136 mol) is dissolved in Et2O (25 ml). At −70° C., a 1.5 M solution of t-BuLi in pentane (17 ml, 0.026 mol) is added dropwise. The mixture is stirred 0.3 h at this temperature and 0.75 h at room temperature. A solution of 1-trityl-1H-imidazole-4-carbaldehyde x43 (2 g, 0.00591 mole) in THF (25 ml) is added dropwise at 0° C. The mixture is stirred for 1 h and poured onto ice. HCl is added until the pH is slightly acid (pH: 3-5) and the aqueous phase is extracted twice with Et2O. The combined organic phases are dried over MgSO4, filtered and concentrated to dryness. The crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 95/4.5/0.5 (v/v/v)) to afford 1.21 g of 1-(1-trityl-1H-imidazol-4-yl)propan-1-ol x88.

後処理

  1. stirringThe mixture is stirred for 1 h
  2. additionpoured onto ice
  3. extractionthe aqueous phase is extracted twice with Et2O
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 95/4.5/0.5 (v/v/v))

出典と根拠

ORDレコード
ord-9c89b3593f4d4e41af7d807c6baa6eda
出典データセット
uspto-grants-2012_05
特許番号
US08178533B2

反応ノート

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