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

HRID 589190
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HRID 589190 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 214805922-((Tert-butyldimethylsilyloxy)methyl)thiazoleHCID 178418306HCID 178418306, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
-78 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-481e3b87cacc44ddbbcc93050697583b
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09227971B2

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