Sodium Cyanide → 8-t-Butyl-3-cyano-1-oxaspiro(4,5)decane
反応式
[C:1]([CH:5]1[CH2:25][CH2:24][C:8]2([O:12][CH2:11][CH:10](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C-:26]#[N:27].[Na+]>CN(C=O)C>[C:1]([CH:5]1[CH2:6][CH2:7][C:8]2([O:12][CH2:11][CH:10]([C:26]#[N:27])[CH2:9]2)[CH2:24][CH2:25]1)([CH3:2])([CH3:3])[CH3:4]参加物
4
反応条件
- 温度
- 100 °C
実験手順
A mixture of 8-t-butyl-3-(p-toluenesulfonyloxy)-1-oxaspiro-(4,5)decane (18.3 g, 50 mmol) and sodium cyanide (4.9 g, 100 mmol) in dry DMF (75 ml) was heated to 100° C. for 6 hours. Light petroleum/ethylacetate 4:1 (50 ml) was added and the mixture was filtrated from insoluble material. The filtrate was then evaporated in vacuo and the resulting residue was taken up in toluene (100 ml). It was washed with water, dried (MgSO4) and evaporated in vacuo to yield a brownish oil (11.0 g) which was Kugelrohr distilled (120°-125° C., 0.015 mbar) to furnish the product as colourless crystals (8.94 g, m.p. 35°-40° C.).