4-(Bromomethyl)benzonitrile → HCID 54160280、化合物

HRID 443229ノート

反応式

HRID 443229 の反応式
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[N:6]=[CH:7][N:8]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:40]([C:42]1[CH:49]=[CH:48][C:45]([CH2:46]Br)=[CH:44][CH:43]=1)#[N:41]>C1COCC1>[CH3:1][O:2][C:3](=[O:29])[CH:4]([C:5]1[N:6]=[CH:7][N:8]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)[CH2:46][C:45]1[CH:48]=[CH:49][C:42]([C:40]#[N:41])=[CH:43][CH:44]=1

参加物

5

反応物 3

HCID 869964-(Bromomethyl)benzonitrileHCID 2733832Lithium HexamethyldisilazideHCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

生成物 1

HCID 54160280HCID 54160280、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of 1-(triphenylmethyl)-1H-imidazol-4-ylacetic acid methyl ester (977 mg, 2.55 mmol) in THF (25 ml) was cooled to -78° C. Lithium hexamethyldisilazide (2.68 ml, 2.68 mmol) was added dropwise and the reaction stirred 30 min at -78° C. 4-Cyanobenzyl bromide (500.7 mg, 2.68 mmol) was added and the reaction stirred a furthur 4 hrs at -78° C. and then at -20° C. for 12 hr. The reaction was quenched with water (10 ml) and saturated NaHCO3 solutuon (10 ml) and extracted with EtOAc. The organic extracts were dried (MgSO4) and the solvent evaporated in vacuo. Chromatography of the residue (SiO2, 3% MeOH in CH2Cl2) afforded the product.

後処理

  1. stirringthe reaction stirred a furthur 4 hrs at -78° C.
  2. waitat -20° C. for 12 hr
  3. customThe reaction was quenched with water (10 ml) and saturated NaHCO3 solutuon (10 ml)
  4. extractionextracted with EtOAc
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customthe solvent evaporated in vacuo
  7. customChromatography of the residue (SiO2, 3% MeOH in CH2Cl2) afforded the product

出典と根拠

ORDレコード
ord-0c9b1c59d4674956bfcd606d104b7072
出典データセット
uspto-grants-1999_04
特許番号
US05891889

反応ノート

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