Sodium hydride → 1-(4-Bromopyrid-3-yl)-1-(4-chloropyrid-3-yl)-1-trimethylacetoxymethane
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[Cl:16])[OH:9].[CH3:17][C:18]([CH3:23])([CH3:22])[C:19](Cl)=[O:20].[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[Cl:16])[O:9][C:19](=[O:20])[C:18]([CH3:23])([CH3:22])[CH3:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
0.4 grams of 1-(4-bromopyrid-3-yl)-1-(4-chloropyrid-3-yl)methanol were dissolved in 50 ml of tetrahydrofuran (THF) and cooled to 0° C. One gram of trimethylacetyl chloride was added followed by the portionwise addition of 0.5 grams of sodium hydride (60%) over a period of 15 minutes. The reaction mixture was then allowed to warm to room temperature and then stirred overnight. 50 ml of a saturated ammonium chloride solution were added and then this mixture was extracted twice with ethyl ether. The combined ether extracts were washed with a 5% aqueous solution of potassium carbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 0.5 g of 1-(4-bromopyrid-3-yl)-1-(4-chloropyrid-3-yl)-1-trimethylacetoxymethane as a waxy solid.
Workup
- temperatureto warm to room temperature
- extractionthis mixture was extracted twice with ethyl ether
- washThe combined ether extracts were washed with a 5% aqueous solution of potassium carbonate
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-21456ab13d2a4215a2d56f04353428dd
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05763357
Reaction notes
Loading…