Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | HCID 19011015 | HCID 19011015 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 54553760 | HCID 54553760 | 97.4% |
Reaction Steps
2-Hydroxymethyl-3,4-(dimethylmethylenedioxy)-5-(1-ethoxyethoxy)cyclohexanone (765 mg) was dissolved in 7 ml of dry methylene chloride, and 1.2 ml of triethylamine, 55.6 mg of N,N-dimethylaminopyridine and 520 mg of tert-butyldimethylsilyl chloride were added at 0° C., followed by stirring the mixture at 0° C. for 13 hours. The obtained reaction mixture was poured into 1N hydrochloric acid, and extracted with diethyl ether. The extract was washed with a saturated sodium hydrogen carbonate aqueous solution and then with a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 1.04 g of 2-(tert-butyldimethylsilyloxymethyl)-3,4-(dimethylmethylenedioxy)-5-(1-ethoxyethoxy)cyclohexanone having the following properties.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05334740 |
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| Source dataset | uspto-grants-1994_08 |
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| ORD ID | ord-4378f324346645c796e3620888603d08 |
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| Source note | uspto-grants-1994_08 |
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