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

HRID 1039148

반응식

HRID 1039148 반응식
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]

참가 물질

7

반응물 3

HCID 7687654-(4-Methoxy-phenyl)-2-methyl-thiazoleHCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilaneHCID 178418306HCID 178418306, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-43b4714b1e834389a98d280abefa4705
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552039B2

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