HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 2-(2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(dimethyl(2-methyl-2-propyl)silyloxy)propyl)phenyl)-2-propoxy)tetrahydropyran
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Reactant | Phosphine, triphenyl-, hydrobromide | HCID 517696 | — |
| Reactant | 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(dimethyl(2-methyl-2-propyl)silyloxy)propyl)phenyl)-2-propanol | HCID 53634794 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(dimethyl(2-methyl-2-propyl)silyloxy)propyl)phenyl)-2-propoxy)tetrahydropyran | HCID 53939699 | — |
Reaction Steps
To a 0.2M solution of the tertiary alcohol of Step 4 in CH2Cl2 were added 5 equiv. of dihydropyran and 0.1 equiv. of triphenylphosphonium bromide and the mixture was stirred at reflux for 1 day. Then, the same amount of dihydropyran and triphenylphosphonium bromide were added and the mixture stirred at reflux another day. Toluene was added and the resulting solution was filtered through silica with EtOAc:toluene 0:100 to 2:98 to afford the title product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05856322 |
| Source dataset | uspto-grants-1999_01 |
| ORD ID | ord-8d250cb1a2c547de9e97ae7b9dfbf062 |
| Source note | uspto-grants-1999_01 |