Imidazole → (5-Bromothiophen-2-yl)methyl Tert-butyldiphenylsilyl Ether

HRID 1071337노트

반응식

HRID 1071337 반응식
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19][C:20]1[S:24][C:23]([CH2:25][OH:26])=[CH:22][CH:21]=1.CN(C)C=O.N1C=CN=C1>CCOCC>[Si:1]([O:26][CH2:25][C:23]1[S:24][C:20]([Br:19])=[CH:21][CH:22]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 11435467(5-Bromothiophen-2-yl)methanol

생성물 1

HCID 22393098(5-Bromothiophen-2-yl)methyl Tert-butyldiphenylsilyl Ether

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Tert-butyldiphenylsilyl chloride (7.8 mL, 30.1 mmol) was added to a solution of 5-bromo(thiophen-2-yl)methyl alcohol (4.9 g, 25.1 mmol) and 9.7 mL of dimethylformamide. The solution was treated with imidazole (4.29 g, 62.8 mmol) and stirred overnight at room temperature. The solution was diluted with ether and washed with 2% aqueous HCl. The layers were separated and the aqueous layer was extracted with ether. The combined organic extracts were washed with brine, and dried (MgSO4), and filtered, and the solvents were removed in vacuo. The residue was purified by silica gel chromatography (hexane) to produce the title compound.

후처리

  1. washwashed with 2% aqueous HCl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvents were removed in vacuo
  8. customThe residue was purified by silica gel chromatography (hexane)

출처 및 근거

ORD 기록
ord-fa3cee793f82499eb74e7d8171c9a046
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06906057B1

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