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

HRID 222569ノート

反応式

HRID 222569 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 19869614Ether dimethylsulfoxide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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)]

出典と根拠

ORDレコード
ord-de96c31730694fe89a71736960f15ef6
出典データセット
uspto-grants-2012_06
特許番号
US08207329B2

反応ノート

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