Methallyl alcohol → HCID 17979076, compound
Reaction equation
[H-].[Na+].[CH3:3][C:4](=[CH2:7])[CH2:5][OH:6].[CH2:8]([O:12][C:13]1[CH:18]=[C:17](Cl)[N:16]=[CH:15][N:14]=1)[C:9]#[C:10][CH3:11].[Cl-].[NH4+]>O1CCCC1>[CH2:8]([O:12][C:13]1[CH:18]=[C:17]([O:6][CH2:5][C:4]([CH3:3])=[CH2:7])[N:16]=[CH:15][N:14]=1)[C:9]#[C:10][CH3:11]Participants
Procedure
In 4 ml of tetrahydrofuran was suspended 0.11 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.16 g of 2-methyl-2-propenol in tetrahydrofuran was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.5 ml of a solution containing 0.4 g of 4-(2-butynyloxy)-6-chloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.15 g of 4-(2-butynyloxy)-6-(2-methylallyloxy)pyrimidine.
Workup
- additionwas added dropwise at 0° C.
- stirringby stirring at the same temperature for 2 hours
- extractionwas extracted three times with t-butyl methyl ether
- washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-689b470323ad4439ad2f11b1d517daa9
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223769B2
Reaction notes
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