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

HRID 1281231Notes

Reaction equation

HRID 1281231 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-084d308304704679b7f195e5c6b58c0f
Source dataset
uspto-grants-2002_09
Patent number
US06452032B1

Reaction notes

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