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Borane;tetrahydrofuran → 2-(1-Trityl-1H-imidazol-4-yl)ethanol

HRID 923243
ノート
印刷プレビュー

反応式

HRID 923243 の反応式
[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][C:26](O)=[O:27])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1.C(CN)O.CCOC(C)=O>[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][OH:27])[N:22]=[CH:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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

6

反応物 2

HCID 2723981Borane;tetrahydrofuranHCID 11090087(1-Trityl-1H-imidazol-4-yl)acetic acid

生成物 1

HCID 106894902-(1-Trityl-1H-imidazol-4-yl)ethanol

試薬・触媒・溶媒 3

HCID 700Ethanolamine溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

(1-Trityl-1H-imidazol-4-yl)acetic acid (65 g, 0.17 mol) is suspended in THF (400 mL) and cooled to 0° C. To this is added BH3.THF solution (350 mL, 1.0 M). The clear solution obtained is stirred at 0° C. for 30 min before warming to room temperature until LCMS indicated completion of the reaction. The solution is cooled again to 0° C. and quenched carefully with water (250 mL). The resulting solution is diluted with EtOAc (300 mL) and transferred to a separatory funnel and the aqueous layer is extracted with EtOAc. The organic phase is dried over anhydrous Na2SO4 and evaporated to give a sticky residue which is taken up in ethanolamine (800 mL) and heated to 90° C. for 2 h. The reaction is transferred to a separatory funnel, diluted with EtOAc (1 L) and washed with water (3×600 mL). The organic phase is dried over anhydrous Na2SO4 and evaporated to give 2-(1-trityl-1H-imidazol-4-yl)-ethanol as a white solid that is used as is without further purification. MS (ESI) m/z 354.8 (M+H) (prepared by alternate method in J. Med. Chem. 1996, 39(19), 3806)

後処理

  1. customThe clear solution obtained
  2. temperaturebefore warming to room temperature until LCMS
  3. customcompletion of the reaction
  4. temperatureThe solution is cooled again to 0° C.
  5. customquenched carefully with water (250 mL)
  6. additionThe resulting solution is diluted with EtOAc (300 mL)
  7. customtransferred to a separatory funnel
  8. extractionthe aqueous layer is extracted with EtOAc
  9. dry with materialThe organic phase is dried over anhydrous Na2SO4
  10. customevaporated
  11. customto give a sticky residue which
  12. temperatureheated to 90° C. for 2 h
  13. customThe reaction is transferred to a separatory funnel
  14. washwashed with water (3×600 mL)
  15. dry with materialThe organic phase is dried over anhydrous Na2SO4
  16. customevaporated

出典と根拠

ORDレコード
ord-037766f0a5ec41a6b7621a4942eb29fe
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278969B2

反応ノート

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