Imidazole → Tert-butyldimethyl(3-(thiophen-2-yl)propoxy)silane

HRID 629154Notes

Reaction equation

HRID 629154 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][OH:9].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].O>ClCCl>[C:18]([Si:15]([CH3:17])([CH3:16])[O:9][CH2:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 131098663-(Thiophen-2-yl)propan-1-ol

Product 1

HCID 131735363Tert-butyldimethyl(3-(thiophen-2-yl)propoxy)silaneYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(thiophene-2-yl)propanol (500 mg, 3.52 mmol) and imidazole (288 mg, 4.22 mmol) in 9 mL anhydrous dichloromethane was added TBS-Cl (584 mg, 3.87 mmol). The resulting mixture was stirred at room temperature for 30 minutes and poured into 50 mL water. Organics were extracted with ether (2×40 mL), dried over magnesium sulfate, filtered and concentrated. The crude oil was subjected to chromatography on silica gel with gradient elution (1-2% ethyl acetate in hexanes) to give tert-butyldimethyl(3-(thiophen-2-yl)propoxy)silane (787 mg, 87%). Used without further characterization.

Workup

  1. extractionOrganics were extracted with ether (2×40 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe crude oil was subjected to chromatography on silica gel with gradient elution (1-2% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-908108efb3944a098dab0df57f4bcd5a
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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