Hydrochloric Acid → 1-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-cyanopyrrole

HRID 850188ノート

反応式

HRID 850188 の反応式
[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:32])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[CH:28]2)[CH:23]=[CH:24][C:25]=1[Cl:26])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClS([N:37]=[C:38]=O)(=O)=O.CN(C)C=O.Cl>ClCCl>[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:32])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[C:28]2[C:38]#[N:37])[CH:23]=[CH:24][C:25]=1[Cl:26])([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 183219091-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)pyrrole

生成物 1

HCID 183218191-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-cyanopyrrole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

NMR (CDCl3, δ): 1.06 (9H, s), 4.98 (2H, s), 6.32 (2H, d, J=4 Hz), 6.83 (2H, d, J=4 Hz), 7.22 (1H, d, J=10 Hz), 7.32-7.48 (7H), 7.74 (4H, d, J=8 Hz) (2) To a solution of 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]pyrrole (1.20 g) in anhydrous dichloromethane (12 ml) was added a solution of chlorosulfonyl isocyanate (0.28 ml) in anhydrous dichloromethane (2.8 ml) dropwise in a dry ice-carbon tetrachloride bath. The mixture was stirred at the same temperature for 30 minutes and then at ambient temperature for additional 1 hour. Anhydrous dimethylformamide (0.4 ml) was added to this mixture dropwise in a dry ice-carbon tetrachloride bath. After stirring at the same temperature for 30 minutes and at ambient temperature for additional 1 hour, the reaction mixture was treated with 4N-hydrochloric acid under ice-water cooling for 30 minutes. The organic layer was isolated and the aqueous layer was extracted with chloroform twice. The combined organic phases were washed with saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluted with n-hexane--ethyl acetate to give 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]-2-cyanopyrrole (930 mg) as a pale yellow oil.

後処理

  1. waitat ambient temperature for additional 1 hour
  2. stirringAfter stirring at the same temperature for 30 minutes and at ambient temperature for additional 1 hour
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer was extracted with chloroform twice
  5. washThe combined organic phases were washed with saturated aqueous sodium hydrogen carbonate
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by a silica gel column chromatography
  9. washeluted with n-hexane

出典と根拠

ORDレコード
ord-87614dd8b7034c088b8236a62869e8df
出典データセット
uspto-grants-2000_01
特許番号
US06015818

反応ノート

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