Sodium Sulfate → {1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}methanol

HRID 2264626노트

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HRID 2264626 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:20](OCC)=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].C1(C)C=CC=CC=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[CH2:20][OH:21])(=[O:9])=[O:10])=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 24436Sodium SulfateHCID 62649Sodium sulfate decahydrateHCID 67043967ethyl 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carboxylateHCID 86595848Hydride toluene

생성물 1

HCID 67044165{1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}methanol수율 77.2%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
-70 °C

실험 절차

To a solution of 1.4 g of ethyl 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carboxylate in 10 mL of THF, 7.6 mL of diisobutylalminum hydride-toluene solution was added at a temperature of −60° C. or lower, and the resulting mixture was stirred under cooling in a dry ice-acetone bath for 5 hours and under ice cooling for 2 hours. After the solution was cooled to −70° C., 5 g of sodium sulfate decahydrate and 5 mL of methanol were added, the resulting mixture was warmed to room temperature, 50 mL of ethyl acetate and anhydrous sodium sulfate were added, insoluble matter was removed by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to obtain 0.97 g of {1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}methanol as a pale violet solid. EI: 365, 367

후처리

  1. temperatureunder cooling in a dry ice-acetone bath for 5 hours and under ice cooling for 2 hours
  2. temperaturethe resulting mixture was warmed to room temperature
  3. custominsoluble matter was removed by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform)

출처 및 근거

ORD 기록
ord-15f54747040349eea6a878198eab5a52
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855225B2

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