Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (2-Bromoethoxy)-tert-butyldimethylsilane | HCID 3608067 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 15159186 | HCID 15159186 | 63% |
Reaction Steps
To 86.4 mg (2.2 mmoles) of 61.1% sodium hydride mineral oil dispersion in 5 mL sieve dried DMF at 0° C. was added 136 mg (2.0 mmoles) of imidazole. The mixture was stirred at 0° C. under nitrogen for 15 minutes and 476 mg (2.0 mmoles) of neat t-butyldimethylsilyloxyethyl bromide was added. The ice-water bath was removed and the mixture stirred overnight and it was then partitioned between ether and ice-water. The organic phase was separated, washed thrice with ice-water, dried over sodium sulfate, filtered, and evaporated to give 282.3 mg (63%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05192758 |
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| Source dataset | uspto-grants-1993_03 |
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| ORD ID | ord-b223883a33e44afe9540a333b0416184 |
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| Source note | uspto-grants-1993_03 |
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