Imidazole → HCID 68180760, compound

HRID 2276901Notes

Reaction equation

HRID 2276901 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][S:8][C:4]=2[CH:3]=1.N1C=CN=C1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18].O>ClCCl>[Si:20]([O:1][C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][S:8][C:4]=2[CH:3]=1)([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 88004Benzo(b)thiophene-6-ol

Product 1

HCID 68180760HCID 68180760, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

6-Hydroxybenzothiophene (22, 8.55 g, 56.9 mmol) and imidazole (4.65 g, 68.3 mmol) were dissolved in dichloromethane (120 mL) and TBDMS-Cl (9.73 g, 62.6 mmol) dissolved in dichloromethane (50 mL) was slowly added at 0° C. The reaction mixture was agitated at 0° C. for 1 hour. After adding water and transferring the resulting solution to a separatory funnel, the dichloromethane layer was separated. The remaining organic compound was extracted three times with dichloromethane. After removing water using sodium sulfate, the solvent was removed under reduced pressure. Column chromatography yielded 6-(t-butyldimethylsilyloxy)benzothiophene (23, 13.6 g, 90%) as a liquid.

Workup

  1. additionwas slowly added at 0° C
  2. customthe dichloromethane layer was separated
  3. extractionThe remaining organic compound was extracted three times with dichloromethane
  4. customAfter removing water
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-caf75de13edc4298b608b8bc36f9e609
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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