反应详情

温度

-78 °C

Sodium amide (0.35 g, 0.009 mole), dry THF (25 mL), and phenylacetylene (0.92 g, 0.009 mole) were placed in a 100 mL, three-necked round-bottomed flask under nitrogen. The reaction was heated at reflux while nitrogen was blown through the flask until ammonia evolution ceased. The reaction slurry was cooled to -78° C., then added to a mixture of benzoquinone (0.97 g, 0.009 mole) in THF (50 mL) at about -108° C. The reaction mixture was allowed to warm to -30° C., then quenched into a saturated solution of ammonium chloride and extracted with ether. The ether extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was chromatographed as in Example 3 to yield 0.05 g (2.6%) of the title carbinol.

1. temperatureThe reaction was heated
2. temperatureat reflux while nitrogen
3. temperatureto warm to -30° C.
4. customquenched into a saturated solution of ammonium chloride
5. extractionextracted with ether
6. dry with materialThe ether extracts were dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was chromatographed as in Example 3
10. customto yield 0.05 g (2.6%) of the title carbinol