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4-Cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketone → 1-(4-Cyano-3-fluorophenyl)-1-[1-(triphenylmethyl)imidazol-4-yl]ethanol

HRID 2306216
ノート
印刷プレビュー

反応式

HRID 2306216 の反応式
[C:1]1([C:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:8]2[CH:12]=[C:11]([C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([F:23])[CH:16]=3)=[O:14])[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:36][Mg+].[Br-]>C1COCC1.CCOCC>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:13]([C:11]2[N:10]=[CH:9][N:8]([C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:12]=2)([OH:14])[CH3:36])=[CH:16][C:17]=1[F:23])#[N:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 545629854-Cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketoneHCID 178418689HCID 178418689、化合物

生成物 1

HCID 184336071-(4-Cyano-3-fluorophenyl)-1-[1-(triphenylmethyl)imidazol-4-yl]ethanol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketone, as described above in Step B, (7.0 g, 15.3 mmol) in dry THF (280 mL), under argon, at −78° C., was added MeMgBr (5.3 mL of a 3.0M solution in Et2O, 15.9 mmol), dropwise. After 1 hour, the reaction mixture was quenched with saturated aqueous NH4Cl (100 mL) and extracted with CH2Cl2 (2×150 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of hexane—30% to 50% EtOAc, to yield the titled product as pale solid.

後処理

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl (100 mL)
  2. extractionextracted with CH2Cl2 (2×150 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a gradient of hexane—30% to 50% EtOAc

出典と根拠

ORDレコード
ord-888fff0c422440cd97748750263c55c0
出典データセット
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06441017B1

反応ノート

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