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

HRID 850188노트

반응식

HRID 850188 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-87614dd8b7034c088b8236a62869e8df
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06015818

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