반응 #1833
ord-ead516c1b5b84915b6f58d3f44f1f181
반응 방정식
반응 조건
후처리
- 1기타the exothermic reaction
- 2온도The reaction mixture was heated
- 3온도at reflux for 18 hours
- 4온도cooled
- 5세척washed with 200 mL of 2N aqueous hydrochloric acid and 200 mL of water
- 6기타The organic layer was removed
- 7여과filtered through Celite
- 8건조dried over magnesium sulfate
- 9여과filtered
- 10기타solvents removed under vacuum
- 11기타Crystallization of the crude residue from cold hexanes
실험 절차
Methylmagnesium chloride solution in tetrahydrofuran (100 mL, 3.0M, 300 mmol) at room temperature was treated dropwise over 30 minutes with a solution of 32.3 g (300 mmol) of p-cresol in 30 mL of tetrahydrofuran. An additional 70 mL of tetrahydrofuran was added to moderate the exothermic reaction. The mixture was aged at room temperature for 2 hours then treated with 400 mL of toluene, 41mg of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and 23 g of paraformaldehyde. The reaction mixture was heated at reflux for 18 hours, then cooled and washed with 200 mL of 2N aqueous hydrochloric acid and 200 mL of water. The organic layer was removed, filtered through Celite, dried over magnesium sulfate, filtered and solvents removed under vacuum. Crystallization of the crude residue from cold hexanes gave 7.4 g (54 mmol, 18%) of the product. The mother liquors were further purified by column chromatography on silica gel, eluting with methylene chloride, to give an additional 17.5 g (128 mmol, 43%) of the product. 1H NMR (200 MHz,CDCl3): 2.33 (s,3H), 6.89 (d,10 Hz,1H), 7.33 (m,2H), 9.83 (s,1H), 10.80 (s,1H).