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

HRID 1618520노트

반응식

HRID 1618520 반응식
[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

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydride2회HCID 25517Ammonium ChlorideHCID 67284396Methyl 2-(5-bromo-3-nitropyridin-2-yl)acetate

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fdaaa6832b9d4c3c9cf48e3ab957baab
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765940B2

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