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Tributyltin Chloride → 2-((Tert-butyldimethylsilyloxy)methyl)-5-(tributylstannyl)thiazole

HRID 589190
ノート
印刷プレビュー

反応式

HRID 589190 の反応式
[Si:1]([O:8][CH2:9][C:10]1[S:11][CH:12]=[CH:13][N:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]C(C)(C)C.[Sn:20](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24].[NH4+].[Cl-]>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[S:11][C:12]([Sn:20]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][N:14]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 214805922-((Tert-butyldimethylsilyloxy)methyl)thiazoleHCID 178418306HCID 178418306、化合物

生成物 1

HCID 672943522-((Tert-butyldimethylsilyloxy)methyl)-5-(tributylstannyl)thiazole収率 77.7%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
-78 °C

実験手順

2-((tert-butyldimethylsilyloxy)methyl)thiazole (8.0 g, 35 mmol) was dissolved in dry THF (350 mL) and the solution was cooled to −78° C. To this solution, t-BuLi (1.7 M, 25 mL, 42 mmol) was added dropwise. The reaction was warmed to −40° C. and stirred for 2 hours. Then, Bu3SnCl (14.6 g, 45 mmol) was added and the resulting mixture was allowed to warm to room temperature slowly and stirred for another 30 min. NH4Cl (aq.) was added to quench the reaction and extracted with EtOAc. The organics was dried and concentrated. The residue was purified with column (silica gel, 0˜30 EtOAc/hexane) to give the product 2-((tert-butyldimethylsilyloxy)methyl)-5-(tributylstannyl)thiazole (14.1 g)

後処理

  1. temperatureThe reaction was warmed to −40° C.
  2. temperatureto warm to room temperature slowly
  3. stirringstirred for another 30 min
  4. customto quench
  5. customthe reaction
  6. extractionextracted with EtOAc
  7. customThe organics was dried
  8. concentrationconcentrated
  9. customThe residue was purified with column (silica gel, 0˜30 EtOAc/hexane)

出典と根拠

ORDレコード
ord-481e3b87cacc44ddbbcc93050697583b
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09227971B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート