Sodium hydride → HCID 67714325, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[OH:9].[CH3:15][C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18].[H-].[Na+].[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[O:9][C:17](=[O:18])[C:16]([CH3:21])([CH3:20])[CH3:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2.0 g of 1-(4-chloropyrid-3-yl)-1-(thien-2-yl)methanol were dissolved in 100 ml of THF and the solution was cooled to 0° C. 3.2 g of trimethylacetyl chloride were added followed by the portionwise addition of 1.0 g of sodium hydride (60%) over a period of 15 minutes. The reaction mixture was allowed to warm to room temperature and then stirred overnight. 100 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 then concentrated in vacuo to obtain 2.7 g of crude product. This material was then purified via chromatography on a silica gel column using ethyl acetatehexane (1:1) as the eluant to afford 1.9 g of 1-(4-chloropyrid-3-yl)-1-(thien-2-yl)-1-trimethylacetoxymethane as an oil.
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
- customto obtain 2.7 g of crude product
- customThis material was then purified via chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-8f78618ea3e34cb9bd0afc5e3d29d9a1
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05595958
Reaction notes
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