Diisopropylethylamine → 5-Tert-butyl-2-methoxy-3-nitrobenzonitrile

HRID 1181926ノート

反応式

HRID 1181926 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:8]([OH:13])=[C:9]([CH:12]=1)[C:10]#[N:11])([CH3:4])([CH3:3])[CH3:2].[CH:17](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C>CO.C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:8]([O:13][CH3:17])=[C:9]([CH:12]=1)[C:10]#[N:11])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 589806535-Tert-butyl-2-hydroxyl-3-nitro-benzonitrile

生成物 1

HCID 508831995-Tert-butyl-2-methoxy-3-nitrobenzonitrile収率 99.9%

試薬・触媒・溶媒 1

HCID 21959252Acetonitrile methanol溶媒

実験手順

The above nitrile (0.5 g, 2.27 mmol) was taken up in 1:9 methanol/acetonitrile (20 mL). N,N-diisopropylethylamine (1.1 mL, 6.35 mmol) was added dropwise followed by (trimethylsilyl)diazomethane (3.2 mL, 6.35 mmol). The reaction was stirred until the bubbling stopped (20 min) and the reaction was quenched with water. The water was extracted 3× with methylene chloride, dried over Na2SO4, filtered, and concentrated in vacuo to give 5-tert-butyl-2-methoxy-3-nitro-benzonitrile (0.531 g, 99%) as a yellow solid.

後処理

  1. custom(20 min)
  2. customthe reaction was quenched with water
  3. extractionThe water was extracted 3× with methylene chloride
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eaae38b0452b44629a10b48db7c58303
出典データセット
uspto-grants-2007_10
特許番号
US07285545B2

反応ノート

読み込み中…