2-Butene, 1-bromo- → Methyl 3-[3-t-butylthio-1-(4-chlorobenzyl)-4-crotyl-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

HRID 1590109ノート

反応式

HRID 1590109 の反応式
[C:1]([S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:7]=1[CH2:24][C:25]([CH3:31])([CH3:30])[C:26]([O:28][CH3:29])=[O:27])([CH3:4])([CH3:3])[CH3:2].[CH2:32](Br)[CH:33]=[CH:34][CH3:35]>CC1C=CC(C)=CC=1.[Cl-].[Cl-].[Zn+2]>[C:1]([S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[C:13]=2[CH2:32][CH:33]=[CH:34][CH3:35])[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:7]=1[CH2:24][C:25]([CH3:31])([CH3:30])[C:26]([O:28][CH3:29])=[O:27])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 1224142-Butene, 1-bromo-HCID 14980577Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoate

生成物 1

HCID 54549141Methyl 3-[3-t-butylthio-1-(4-chlorobenzyl)-4-crotyl-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 7809P-Xylene溶媒

実験手順

To a suspension of KH (35% dispersion in oil, 547 mg, 4.78 mmol) in p-xylene (20 mL) there was added methyl 3-[3-tert-butylthio-1-(4-chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate from Example 1, Method A, Step 3 (2.0 g, 4.35 mmol) and the mixture was refluxed for 20 minutes; after cooling, there was added freshly fused ZnCl2 (68 mg, 0.5 mmol) and the mixture was again refluxed for one hour, then cooled down to r.t. To the solution was added crotyl bromide (882 mg, 6.53 mmol) and stirring was continued at room temperature overnight. The mixture was quenched with saturated aqueous NH4Cl (20 mL) and 2 mL of 1N HCl. The organic phase was collected and the aqueous phase extracted with EtOAc. The combined organic phases were washed with H2O 3 times, dried and evaporated. The residue was chromatographed to afford the title compound as the minor component, as a yellow oil.

後処理

  1. temperaturethe mixture was refluxed for 20 minutes
  2. temperatureafter cooling
  3. temperaturethe mixture was again refluxed for one hour
  4. customThe mixture was quenched with saturated aqueous NH4Cl (20 mL) and 2 mL of 1N HCl
  5. customThe organic phase was collected
  6. extractionthe aqueous phase extracted with EtOAc
  7. washThe combined organic phases were washed with H2O 3 times
  8. customdried
  9. customevaporated
  10. customThe residue was chromatographed

出典と根拠

ORDレコード
ord-9359397155bb4c9dbc3fd34480d23ade
出典データセット
uspto-grants-1993_04
特許番号
US05202321

反応ノート

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