Triglyme → 5-{1-[2-(4-Bromo-2-methyl-phenyl)-thiazol-5-yl]-ethoxy}-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

HRID 41673

反応式

HRID 41673 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([OH:15])[CH3:14])=[CH:11][N:12]=2)=[C:4]([CH3:16])[CH:3]=1.Cl[C:18]1[CH:26]2[CH:21]([CH:22]3[O:27][CH:25]2[CH2:24][CH2:23]3)[C:20](=[O:28])[CH:19]=1.[H-].[Na+].COCCOCCOCCOC>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([O:15][C:18]3[CH:26]4[CH:21]([CH:22]5[O:27][CH:25]4[CH2:24][CH2:23]5)[C:20](=[O:28])[CH:19]=3)[CH3:14])=[CH:11][N:12]=2)=[C:4]([CH3:16])[CH:3]=1

参加物

6

反応物 4

HCID 8189TriglymeHCID 24758Sodium hydrideHCID 595846761-[2-(4-Bromo-2-methyl-phenyl)-thiazol-5-yl]-ethanolHCID 685678445-Chloro-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

生成物 1

HCID 687735855-{1-[2-(4-Bromo-2-methyl-phenyl)-thiazol-5-yl]-ethoxy}-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one収率 73.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of [2-(4-bromo-2-methyl-phenyl)-thiazol-5-yl]-ethanol (450 mg, 1.5 mmol) and 5-chloro-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (277 mg, 1.5 mmol) in tetrahydrofuran (10 ml) is added in one portion the sodium hydride (60% dispersion in mineral oil, 60 mg, 1.5 mmol). The reaction mixture is stirred at room temperature for 24 hours. The crude reaction mixture is vacced down under reduced pressure and 10 ml of triglyme are added. The reaction mixture is therefore heated to reflux for 30 minutes. The crude reaction mixture is vacced down and purified by flash chromatography on silica gel to give a yellow solid. The solid is washed with iso-hexane to give 5-{1-[2-(4-bromo-2-methyl-phenyl)-thiazol-5-yl]-ethoxy}-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (490 mg).

後処理

  1. customThe crude reaction mixture
  2. additionare added
  3. temperatureThe reaction mixture is therefore heated
  4. temperatureto reflux for 30 minutes
  5. customThe crude reaction mixture
  6. custompurified by flash chromatography on silica gel
  7. customto give a yellow solid
  8. washThe solid is washed with iso-hexane

出典と根拠

ORDレコード
ord-d1656d9515194173a1d6413fd2f90966
出典データセット
uspto-grants-2013_09
特許番号
US08530667B2

関連ノート

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