HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 67244725, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine | HCID 353442 | — |
| Reactant | Phenol, 2-[(1E)-2-(2-bromophenyl)ethenyl]-4-chloro-, 1-acetate | HCID 44139027 | — |
| Catalyst | Trifluoroacetic acid | HCID 6422 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 67244725 | HCID 67244725 | — |
Reaction Steps
N-benzyl-N-methoxymethyl-N-(trimethylsilylmethyl)amine (5.0 g, 21.06 mmol) was added dropwise with a syringe over 30 minutes to a suspension of (E)-2-(2-bromostyryl)-4-chlorophenyl acetate (Example 1; 7.0 g, 19.9 mmol) in toluene (25 ml) containing trifluoroacetic acid (3 drops) while stirring at room temperature. After additional stirring for one hour water (10 ml) was added. The toluene layer was separated. The aqueous layer was extracted with toluene (25 ml). The combined organic layers were dried with Na2SO4 and evaporated under vacuum to give the crude cycloadduct as a clear and colorless oil, 10.76 g (>100%) in quantitative yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07964739B2 |
| Source dataset | uspto-grants-2011_06 |
| ORD ID | ord-e6441431342a4e2ab9d9546a6e317f4d |
| Source note | uspto-grants-2011_06 |