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Trifluoromethanesulfonic anhydride → 5-Acetoxymethyl-1-[2-(1-adamantyl)ethyl]2-n-butylimidazole

HRID 6486
ノート
印刷プレビュー

反応式

HRID 6486 の反応式
[C:1]12(CCO)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(C(C)C)CC)(C)C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[C:38]([N:41]1[C:45]([CH2:46][O:47][C:48](=[O:50])[CH3:49])=[CH:44][N:43]=[C:42]1[CH2:51][CH2:52][CH2:53][CH3:54])(=O)[CH3:39]>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[C:48]([O:47][CH2:46][C:45]1[N:41]([CH2:38][CH2:39][C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)[C:42]([CH2:51][CH2:52][CH2:53][CH3:54])=[N:43][CH:44]=1)(=[O:50])[CH3:49]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 1108102-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanolHCID 197935471-Acetyl-2-n-butyl 5-acetoxymethyl imidazole

生成物 1

HCID 199367975-Acetoxymethyl-1-[2-(1-adamantyl)ethyl]2-n-butylimidazole

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
3 回
HCID 21584188Chloroform methanol溶媒

実験手順

A mixture of 2-(1-adamantyl)ethanol (10.7 g) and diisopropylethylamine (11 ml) in methylene chloride (70 ml) was added to triflic anhydride (16.75 g) in 70 ml of methylene chloride at -78° C. for 45 minutes, 1-acetyl-2-n-butyl 5-acetoxymethyl imidazole in 50 ml of methylene chloride was added and the mixture was allowed to stand at room temperature for 4 days, then concentrated and heated on a steam bath with 10% sodium hydroxide (250 ml), diluted with 300 ml of water, extracted with methylene chloride, dried, filtered and concentrated to give an oil. Chromatography on silica gel in methanol/chloroform gave 5-acetoxymethyl-1-[2-(1-adamantyl)-ethyl]-2-n-butyl-imidazole. This acetoxy compound (5.4 g) was stirred at room temperature with potassium hydroxide (5.2 g) in ethanol (200 ml) for one hour, the mixture was concentrated, poured into water, stirred, and filtered to give 1-[2-(1-adamantyl)ethyl]-2-n-butyl-5-hydroxymethyl- 1H-imidazole.

後処理

  1. concentrationconcentrated
  2. temperatureheated on a steam bath with 10% sodium hydroxide (250 ml)
  3. additiondiluted with 300 ml of water
  4. extractionextracted with methylene chloride
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil

出典と根拠

ORDレコード
ord-4abdcb5f4ce64f6f9dc993a5b72d5eb7
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05248689

反応ノート

読み込み中…

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