HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilyl triflate → Methyl 1,4-dioxaspiro[4.5]decane-7-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilyl triflate | HCID 65367 | — |
| Reactant | 2,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctane | HCID 81858 | — |
| Reactant | Methyl 3-oxocyclohexane-1-carboxylate | HCID 566099 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 1,4-dioxaspiro[4.5]decane-7-carboxylate | HCID 372311 | — |
Reaction Conditions
| Temperature | -78 °C |
|---|
Reaction Steps
To a solution of trimethylsilyltrifluoromethanesulfonate (0.034 mL) in dry dichloromethane (5 mL) was added 1,2-bis(trimethylsiloxy)ethane (4.55 mL) followed by methyl 3-oxocyclohexanecarboxylate (2.9 g). The reaction mixture was stirred for 3 hours at −78° C. The reaction mixture was quenched with dry pyridine (0.5 mL), poured into saturated aqueous NaHCO3, and extracted with ether. The ether layer was dried over Na2CO3/Na2SO4. The reaction mixture was concentrated and purified by flash chromatography on silica with 5 to 30% ethyl acetate in hexanes to provide the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08580794B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-9050507d09314ffca3406ac1c87e0adb |
| Source note | uspto-grants-2013_11 |