HuagongsheHuagongshe Chemistry Print Report · For research reference only
Imidazole → [5-Bromo-1-(1-propylcyclobutyl)pent-3-enyloxy]tert-butyldimethylsilane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Bromine | HCID 24408 | — |
| Reactant | 5-(Tert-butyldimethylsilanyloxy)-5-(1-propylcyclobutyl)pent-2-en-1-ol | HCID 67102120 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | [5-Bromo-1-(1-propylcyclobutyl)pent-3-enyloxy]tert-butyldimethylsilane | HCID 67101903 | 86.5% |
Reaction Steps
Bromine (0.17 mL, 3.22 mmol) was added to a solution of triphenylphosphine (844 mg, 3.22 mmol) and imidazole (219 mg, 3.22 mmol) in CH2Cl2 (11.0 mL) at 23° C. After 0.5 h a solution of the alcohol 7 (838 mg, 2.68 mmol) in CH2Cl2 (2.7 mL) was added. The reaction was stirred for 1 h, diluted with hexane and then filtered through celite. The filtrate was concentrated in vacuo and purified by FCC (silica gel, 100% hex) to give 870 mg (86%) of the bromide 8 as a clear, light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07314890B2 |
| Source dataset | uspto-grants-2008_01 |
| ORD ID | ord-c85713b7e4ee41cea91b1e15a54ab977 |
| Source note | uspto-grants-2008_01 |