4-(4-Methoxy-phenyl)-2-methyl-thiazole → 2-[7-(Tert-butyldimethylsilanyloxy)heptyl]-4-(4-methoxyphenyl)thiazole

HRID 1039148ノート

反応式

HRID 1039148 の反応式
C([Li])(C)(C)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)=[CH:10][CH:9]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>O1CCCC1.[NH4+].[Cl-].[Cl-].[Na+].O>[Si:28]([O:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:19][C:16]1[S:17][CH:18]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)[N:15]=1)([C:31]([CH3:32])([CH3:33])[CH3:34])([CH3:30])[CH3:29]

参加物

7

反応物 3

HCID 7687654-(4-Methoxy-phenyl)-2-methyl-thiazoleHCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilaneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 684899302-[7-(Tert-butyldimethylsilanyloxy)heptyl]-4-(4-methoxyphenyl)thiazole収率 61.2%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

Add a solution of tert-butyllithium (26.35 mmol, 15.5 mL, 1.7 M in hexanes) dropwise to a solution of 4-(4-methoxyphenyl)-2-methylthiazole (6.15 g, 29.9 mmol) in degassed anhydrous tetrahydrofuran (THF) (100 mL) at −78° C. under nitrogen and stir the solution for 45 minutes. To this solution, add a solution of (6-bromohexyloxy)-tert-butyldimethylsilane (7.20 g, 24.4 mmol) over 5 min and stir the mixture for 2 hours. Warm the mixture to 0° C., dilute with NH4Cl (200 mL) and brine (250 mL) and extract with methylene chloride (3×150 mL). Dry the combined organic extracts over magnesium sulfate and remove the solvent under reduced pressure. Purify the crude product by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (5:1), to provide 2-[7-(tert-butyldimethylsilanyloxy)heptyl]-4-(4-methoxyphenyl)thiazole (6.27 g, 50%).

後処理

  1. stirringstir the mixture for 2 hours
  2. extractionextract with methylene chloride (3×150 mL)
  3. dry with materialDry the combined organic extracts over magnesium sulfate
  4. customremove the solvent under reduced pressure
  5. customPurify the crude product by flash column chromatography on silica gel
  6. washeluting with hexanes/ethyl acetate (5:1)

出典と根拠

ORDレコード
ord-43b4714b1e834389a98d280abefa4705
出典データセット
uspto-grants-2013_10
特許番号
US08552039B2

反応ノート

読み込み中…