HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-Benzyloxyethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- | HCID 18462 | — |
| Reactant | 4-Benzyloxy-2,2-dihydroxymethylbutanol | HCID 53796234 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | 5-Benzyloxyethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane | HCID 90300365 | 164% |
Reaction Steps
543 mg of the crude 4-benzyloxy-2,2-dihydroxymethylbutanol product was dissolved in 3 mL of acetone, 232 mg (1.0 mmol equivalents) of 10-camphorsulfonic acid was added thereto, and a reaction was carried out at room temperature (25° C.) overnight. After completion of the reaction, triethylamine was added dropwise, and the mixture was concentrated under vacuum. The crude product thus obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1) to give 459 mg (1.64 mmol equivalents) of 5-benzyloxyethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09107964B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-8823c723f4fd494f804d0fb5717bd8cf |
| Source note | uspto-grants-2015_08 |