Imidazole → 2-[(Tert-butyldimethylsilyl)oxy]-5-chloroaniline

HRID 1827865ノート

反応式

HRID 1827865 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C>[Si:10]([O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[NH2:1])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

参加物

5

反応物 3

HCID 795ImidazoleHCID 72652-Amino-4-chlorophenolHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 695922282-[(Tert-butyldimethylsilyl)oxy]-5-chloroaniline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2-amino-4-chlorophenol (14.3 g, 100 mmol), tert-butyldimethylsilyl chloride (18 g, 120 mmol) and imidazole (14 g, 200 mmol) in DMF (250 mL) was stirred at room temperature for 24 hours, concentrated, and partitioned between brine (300 mL) and ethyl acetate (300 mL). The aqueous phase was extracted with ethyl acetate. The combined phases were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 15% ethyl acetate/hexanes to provide 18.5 g (71.7% )of the desired product. MS (DCI/NH3) m/z 258 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 6.70 (d, J=2.71 Hz, 1H), 6.64 (d, J=8.5 Hz, 1H), 6.57 (dd, J=2.7 and 8.5 Hz, 1H), 3.75 (br s, 2H), 1.01 (s, 9H), 0.23 (s, 6H).

後処理

  1. concentrationconcentrated
  2. custompartitioned between brine (300 mL) and ethyl acetate (300 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 15% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-0a4ed8a617944d6ba509fa0ecb864c67
出典データセット
uspto-grants-2006_06
特許番号
US07056925B2

反応ノート

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