Water → Ethyl 5-bromo-2-formyl-1-(2-trimethylsilylethoxymethyl)-1H-pyrrol-3-carboxylate

HRID 2097485노트

반응식

HRID 2097485 반응식
[Br:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([CH2:15][O:16]C)=[C:4]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:3]=1.ClCCl.O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:12])[CH3:13])[C:5]([CH:15]=[O:16])=[C:4]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6344DichloromethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 66602785ethyl 5-bromo-2-methoxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-pyrrol-3-carboxylate

생성물 1

HCID 86627038Ethyl 5-bromo-2-formyl-1-(2-trimethylsilylethoxymethyl)-1H-pyrrol-3-carboxylate수율 99.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To 450 g (1.15 mol) of ethyl 5-bromo-2-methoxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-pyrrol-3-carboxylate obtained in Reference example 15-(e) were added 5.4 L of dichloromethane and 540 ml of water, and then, 363 g (1.60 mol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was added to the mixture by dividing it into several portions at room temperature. The mixture was stirred at room temperature for 30 minutes, and then, refluxed for 6 hours. After completion of the reaction, 450 g of Celite and 2.5 L of toluene were added to the reaction suspension, the mixture was stirred at room temperature for 30 minutes, and insoluble material was removed by filtration. The organic layer obtained by separating the filtrate was washed successively with a saturated aqueous solution of sodium hydrogencarbonate, and with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 430 g of the title compound as a pale brownish oil substantially quantitatively.

후처리

  1. customat room temperature
  2. temperaturerefluxed for 6 hours
  3. additionwere added to the reaction suspension
  4. stirringthe mixture was stirred at room temperature for 30 minutes
  5. custominsoluble material was removed by filtration
  6. customThe organic layer obtained
  7. customby separating the filtrate
  8. washwas washed successively with a saturated aqueous solution of sodium hydrogencarbonate
  9. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-61e731717ea84c40a84d95f0b9041036
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450319B2

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