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Bis(2-bromoethyl) ether → 4-[N-(diphenylmethylene)amino]tetrahydropyran-4-carboxylic acid benzyl ester

HRID 1596024
ノート
印刷プレビュー

反応式

HRID 1596024 の反応式
[H-].[Na+].[CH2:3]([O:10][C:11](=[O:27])[CH2:12][N:13]=[C:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:29][CH2:30][O:31][CH2:32][CH2:33]Br.C(OCC)(=O)C.CCCCCC>COCCOC>[CH2:3]([O:10][C:11]([C:12]1([N:13]=[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[O:27])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 11782449Diphenylmethylene-Glycine benzyl esterHCID 21226206Ethyl acetate hexane2 回

生成物 1

HCID 537582684-[N-(diphenylmethylene)amino]tetrahydropyran-4-carboxylic acid benzyl ester

試薬・触媒・溶媒 1

HCID 8071
1,2-Dimethoxyethane
溶媒
4 回

実験手順

To a suspension of sodium hydride (6.56 grams. 0.164 mole) in ethylene glycol dimethyl ether (150 mL) at 0° C. is added a solution of the N-(diphenylmethylene)glycine benzyl ester (0.07398 mole) in ethylene glycol dimethyl ether (50 mL) dropwise via addition funnel. A solution of 2-bromoethyl ether (23.21 grams, 0.090 mole) in ethylene glycol dimethyl ether (50 mL) is then added, in 10 mL portions over approximately 5 minutes, to the ethylene glycol dimethyl ether solution. The ice bath is removed and the reaction is stirred at room temperature for 16 hours. The mixture is diluted with diethyl ether and washed with water. The aqueous layer is extracted with diethyl ether. The combined organic extracts are washed with brine, dried over magnesium sulfate, and concentrated to afford crude product. Chromatography on silica gel eluting first with 4 L of 5% ethyl acetate/hexane followed by 4 liters of 10% ethyl acetate/hexane provides 4-[N-(diphenylmethylene)amino]tetrahydropyran-4-carboxylic acid benzyl ester as a clear yellow oil.

後処理

  1. additiondropwise via addition funnel
  2. customThe ice bath is removed
  3. additionThe mixture is diluted with diethyl ether
  4. washwashed with water
  5. extractionThe aqueous layer is extracted with diethyl ether
  6. washThe combined organic extracts are washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto afford crude product

出典と根拠

ORDレコード
ord-b3b5b6c16e08436c8d07128e43d80ec1
出典データセット
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06288246B1

反応ノート

読み込み中…

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