2-Bromopropane → HCID 13840807, 화합물

HRID 653147노트

반응식

HRID 653147 반응식
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[CH3:7][O:8][C:9]([C:11]1[N:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][C:16]([O:21][CH3:22])=[CH:15][CH:14]=2)=[O:10].BrC(C)C>CS(C)=O>[CH3:7][O:8][C:9]([C:11]1[N:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:13]2[C:18]([C:19]=1[O:20][CH:2]([CH3:3])[CH3:1])=[CH:17][C:16]([O:21][CH3:22])=[CH:15][CH:14]=2)=[O:10]

참가 물질

5

반응물 3

HCID 63582-BromopropaneHCID 23665647Potassium tert-butoxideHCID 54696100Methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylate

생성물 1

HCID 13840807HCID 13840807, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

A stirred mixture of 24.8 g (0.22 mole) of potassium tert-butoxide in 100 ml of dimethyl sulfoxide (under a nitrogen atmosphere) was placed in a cold water bath. A solution of 44.6 g (0.15 mole) of 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester [P. C. Unangst and M. E. Carethers, J. Heterocyclic Chem., 21, 709 (1984)] in 100 ml of dimethyl sulfoxide was added over 30 minutes. The new mixture was stirred for an additional 45 minutes, and 25.0 ml (32.8 g, 0.27 mole) of 2-bromopropane was added in one portion. The cooling bath was removed, and the mixture was stirred at room temperature for 45 hours, then added to 2.5 kg ice water. The crude ester intermediate was removed by extracting with dichloromethane (4×800 ml). The combined organic layers were washed with water (1×2.0 l), 5% aqueous sodium bicarbonate (2×2.0 l), and water again (1×2.0 l), before being dried with anhydrous sodium sulfate. Evaporation (vacuum) yielded a crude residue of 5-methoxy-3-(1-methylethoxy)-1-phenyl-1H-indole-2-carboxylic acid methyl ester.

후처리

  1. customwas placed in a cold water bath
  2. customThe cooling bath was removed
  3. stirringthe mixture was stirred at room temperature for 45 hours
  4. additionadded to 2.5 kg ice water
  5. customThe crude ester intermediate was removed
  6. extractionby extracting with dichloromethane (4×800 ml)
  7. washThe combined organic layers were washed with water (1×2.0 l), 5% aqueous sodium bicarbonate (2×2.0 l), and water again (1×2.0 l)
  8. dry with materialbefore being dried with anhydrous sodium sulfate
  9. customEvaporation (vacuum)

출처 및 근거

ORD 기록
ord-98dad10e52424038936cb44a247d37c5
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04675332

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