Hexane → 5-Chloro-3-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2-methoxyphenyl]-3-hydroxy-1,3-dihydro-indol-2-one

HRID 1716790노트

반응식

HRID 1716790 반응식
C([Li])CCC.CCCCCC.I[C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[O:24][CH2:23][C:22]([CH3:26])([CH3:25])[CH2:21][O:20]2)=[CH:15][C:14]=1[O:27][CH3:28].[Na].[Cl:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[NH:36][C:35](=[O:40])[C:34]2=[O:41].ClC1C=C2C(=CC=1)NC(=O)C2=O.[H-].[Na+].[Cl-].[NH4+]>C1COCC1>[Cl:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[NH:36][C:35](=[O:40])[C:34]2([C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[O:24][CH2:23][C:22]([CH3:26])([CH3:25])[CH2:21][O:20]2)=[CH:15][C:14]=1[O:27][CH3:28])[OH:41]

참가 물질

9

반응물 7

HCID 8058HexaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 872035-chloro-1H-indole-2,3-dioneHCID 594689832-(4-Iodo-3-methoxyphenyl)-5,5-dimethyl[1,3]dioxaneHCID 670430655-Chlorisatin sodium saltHCID 178418339Butyllithium

생성물 1

HCID 670433285-Chloro-3-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2-methoxyphenyl]-3-hydroxy-1,3-dihydro-indol-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of n-butyllithium in hexane (1.6 m, 5.52 ml, 8.83 mmol) was slowly added dropwise to a solution of 2-(4-iodo-3-methoxyphenyl)-5,5-dimethyl[1,3]dioxane (3.00 g, 8.62 mmol) in THF (100 ml) at −78° C. After 15 min, a solution of 5-chloroisatin sodium salt [prepared by treating a solution of 5-chloroisatin (1.21 g, 6.64 mmol) in THF with one equivalent of sodium hydride at 0° C. for one h] was added dropwise to the solution of the organolithium species. The reaction mixture is allowed to warm to room temperature and then stirred for one further hour. Aqueous ammonium chloride solution was added to the reaction solution with stirring, and the mixture was extracted with ethyl acetate. The combined organic phase was washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The desired product crystallizes on standing in the cold. Yield: 1.42 g (53%) of a white solid. MS (API-ES, pos) m/z=404 [M+H]+

후처리

  1. stirringwith stirring
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic phase was washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe desired product crystallizes

출처 및 근거

ORD 기록
ord-59c48bf6b57744e58ef37a4d0afa44c1
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803834B2

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