Ethyl 2-(diphenylmethyleneamino)acetate → ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

HRID 454446ノート

反応式

HRID 454446 の反応式
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Cs+].Br[CH2:25][CH:26]=[C:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[C:1]1([C:7](=[N:8][CH:9]([CH2:25][CH:26]=[C:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 219961434-(2-Bromoethylidene)tetrahydro-2H-pyranHCID 23679066Caesium hydroxide--water (1/1/1)

生成物 1

HCID 58313138ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of ethyl N-(diphenylmethylidene)glycinate (5.29 g, 19.8 mmol), benzyltriethylammonium chloride (0.41 g, 1.8 mmol) and cesium hydroxide monohydrate (4.54 g, 27.0 mmol) in anhydrous dichloromethane (50 mL) was added 4-(2-bromoethylidene)tetrahydro-2H-pyran (3.44 g, 18.0 mmol) as a solution in anhydrous dichloromethane (40 mL) and the reaction stirred at room temperature for 72 h under nitrogen. The reaction was partitioned between dichloromethane and water and the aqueous layer was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 5-40% hexanes/EtOAc to afford the title compound as a clear oil in quantitative yield.

後処理

  1. customThe reaction was partitioned between dichloromethane and water
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 5-40% hexanes/EtOAc

出典と根拠

ORDレコード
ord-6dfa388c81714002bc7f914b724ce22e
出典データセット
uspto-grants-2013_07
特許番号
US08492554B2

反応ノート

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