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Imidazole → 3-Imidazol-1-yl-2,2-dimethyl-indan-1-one

HRID 2089519
ノート
印刷プレビュー

反応式

HRID 2089519 の反応式
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(N(C(C)C)CC)(C)C.O[CH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28](=[O:35])[C:27]1([CH3:37])[CH3:36].[NH:38]1[CH:42]=[CH:41][N:40]=[CH:39]1>ClCCl.C([O-])(O)=O.[Na+].C(OCC)(=O)C>[N:38]1([CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28](=[O:35])[C:27]2([CH3:37])[CH3:36])[CH:42]=[CH:41][N:40]=[CH:39]1
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

8

反応物 4

HCID 795ImidazoleHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 130236813-Hydroxy-2,2-dimethyl-1-indanone

生成物 1

HCID 577810843-Imidazol-1-yl-2,2-dimethyl-indan-1-one

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒3 回
HCID 8857Ethyl Acetate溶媒
HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
-78 °C

実験手順

To a solution of trifluoromethansulfonic anhydride (1.13 mL, 6.75 mmol) in dichloromethane (10 mL) at −78° C. is added, via cannula, a solution of diisopropylethylamine (1.8 mL, 10.1 mmol) and 3-hydroxy-2,2-dimethyl-indan-1-one, prepared as described in Example 20, (400 mg, 2.25 mmol) in dichloromethane (5 mL). The reaction is stirred at −78° C. for 10 minutes and then is placed at −10° C. for 10 minutes. The reaction is then re-cooled to −78° C. and a solution of imidazole (920 mg, 13.5 mmol) in dichloromethane (12 mL) is added via cannula. The reaction is then placed at room temperature for 1 hour, at which time it is diluted with saturated aqueous NaHCO3 and ethyl acetate. The layers are separated and the aqueous layer is extracted two times with ethyl acetate. The combined organic layers are dried with MgSO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 1:3 to 1:0), to afford 3-imidazol-1-yl-2,2-dimethyl-indan-1-one; MS: (ESI) m/z 227 (M+H)+; 1H NMR: (400 MHz, CDCl3) δ ppm 0.80 (s, 3 H), 1.41 (s, 3 H), 5.52 (s, 1 H), 6.73 (s, 1 H), 7.12 (s, 1 H), 7.51 (d, J=7.6 Hz, 1 H), 7.56 (s, 1 H), 7.62 (t, J=7.5 Hz, 1 H), 7.70-7.80 (m, 1 H), 7.91 (d, J=7.6 Hz, 1 H).

後処理

  1. waitis placed at −10° C. for 10 minutes
  2. temperatureThe reaction is then re-cooled to −78° C.
  3. waitThe reaction is then placed at room temperature for 1 hour, at which time it
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted two times with ethyl acetate
  6. dry with materialThe combined organic layers are dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 1:3 to 1:0)

出典と根拠

ORDレコード
ord-65c210704e4d4bff922d46d1af3fd77a
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08436035B2

反応ノート

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