Dimethylformamide → ethyl 4-(5-bromo-3-nitropyridin-2-yl)tetrahydro-2H-pyran-4-carboxylate

HRID 1618520ノート

反応式

HRID 1618520 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:19][CH2:20][O:21][CH2:22][CH2:23]Br.[NH4+].[Cl-].[CH3:27]N(C=O)C>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([C:8]2([C:9]([O:11][CH2:12][CH3:27])=[O:10])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[N:6][CH:7]=1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydride2 回HCID 25517Ammonium ChlorideHCID 67284396Methyl 2-(5-bromo-3-nitropyridin-2-yl)acetate

生成物 1

HCID 67285709ethyl 4-(5-bromo-3-nitropyridin-2-yl)tetrahydro-2H-pyran-4-carboxylate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of methyl 2-(5-bromo-3-nitropyridin-2-yl)acetate (2.0 g, 7.27 mmol) in DMF (15 mL) was added sodium hydride (0.384 g, 16.00 mmol) portionwise over 5 min (solution turns dark blue). The reaction was stirred at rt for 15 min and then 2-bromoethyl ether (1.69 mL, 7.27 mmol) was added via syringe over 1 min. The reaction was stirred at rt for 16 h. After this time 0.2 g of NaH was added and the reaction was stirred at rt for 14 h. The reaction was treated with saturated aqueous NH4Cl (60 mL) and EtOAc (300 mL). The separated organic layer was washed with 1.0M aqueous LiCl (60 mL) and then dried over MgSO4, filtered and evaporated in vacuo. Column chromatography (hexane:EtOAc, 1:0 to 1:1) gave ethyl 4-(5-bromo-3-nitropyridin-2-yl)tetrahydro-2H-pyran-4-carboxylate as a dark brown oil.

後処理

  1. stirringThe reaction was stirred at rt for 16 h
  2. stirringthe reaction was stirred at rt for 14 h
  3. washThe separated organic layer was washed with 1.0M aqueous LiCl (60 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-fdaaa6832b9d4c3c9cf48e3ab957baab
出典データセット
uspto-grants-2014_07
特許番号
US08765940B2

反応ノート

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