Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-Iodopropane | HCID 33643 | — |
| Reactant | HCID 19097301 | HCID 19097301 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 54031616 | HCID 54031616 | 20% |
Reaction Steps
1.00 g (3.21 mmol) of Compound G was dissolved in 30 ml of dimethylformamide, and 256 mg of sodium hydride (60%, 6.41 mmol) was added slowly to the solution at 0° C. After 30 minutes, 0.33 ml (3.4 mmol) of 1-iodopropane was added dropwise slowly at the same temperature and stirred at room temperature overnight. The resulting reaction mixture was poured into 300 ml of water, neutralized and extracted three times with 100 ml of chloroform. The organic layer was washed with a saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluate: 30% ethyl acetate/hexane) to give 225 mg (yield 20%) of Compound H as a colorless needle crystal.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05395836 |
|---|
| Source dataset | uspto-grants-1995_03 |
|---|
| ORD ID | ord-d46e074f59d540e2adb5b37dc32404f0 |
|---|
| Source note | uspto-grants-1995_03 |
|---|