Dichloromethane → ethyl 4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate

HRID 222569노트

반응식

HRID 222569 반응식
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[CH3:2].CC1C=CC(S([CH2:27][N+:28]#[C-:29])(=O)=O)=CC=1.[H-].[Na+].C(Cl)Cl>CS(C)=O.CCOCC.CCOCC.[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([C:5]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)=[CH:29][NH:28][CH:27]=1)=[O:16])[CH3:2]

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 95370Ethyl 3-(4-nitrophenyl)-2-propenoateHCID 161915Tosylmethyl isocyanide

생성물 1

HCID 53440113ethyl 4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate수율 84%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 19869614Ether dimethylsulfoxide용매HCID 57417360Sodium chloride; water용매

실험 절차

A solution of 54 (3.74 g, 16.91 mmol) and TosMIC (3.30 g, 16.92 mmol) in DMSO/Et2O (1:2, 33 mL) was added via cannula to a vigorously stirred suspension of NaH (842 mg, 35.1 mmol) in Et2O (15 mL) under argon. Stirring was continued for 3 h. Brine and CH2Cl2 were added in small portions. The aqueous layer was extracted with CH2Cl2. The organic extract was washed with brine. The solvent was removed at reduced pressure, and the oily residue was chromatographed [silica, CH2Cl2/ethyl acetate (9:1)] to yield a brown solid (3.23 g, 84%): 1H NMR δ 1.23-1.29 (m, 3H), 4.20-4.27 (m, 2H), 6.88-6.90 (m, 1H), 7.53-7.55 (m, 1H), 7.64-7.67 (m, 2H), 8.18-8.21 (m, 2H), 8.78 (br, 1H).

후처리

  1. extractionThe aqueous layer was extracted with CH2Cl2
  2. extractionThe organic extract
  3. washwas washed with brine
  4. customThe solvent was removed at reduced pressure
  5. customthe oily residue was chromatographed [silica, CH2Cl2/ethyl acetate (9:1)]

출처 및 근거

ORD 기록
ord-de96c31730694fe89a71736960f15ef6
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207329B2

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