Benzyl Alcohol → 2,4-Bis-benzyloxy-5-tert-butyl-6-chloro-pyrimidine

反応式

[Na].[C:2]([C:6]1[C:7](Cl)=[N:8][C:9](Cl)=[N:10][C:11]=1[Cl:12])([CH3:5])([CH3:4])[CH3:3].[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:15]([O:22][C:9]1[N:8]=[C:7]([O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])=[C:11]([Cl:12])[N:10]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

反応物 3

HCID 244Benzyl Alcohol

HCID 5360545Sodium

HCID 136032625-tert-Butyl-2,4,6-trichloro-pyrimidine

生成物 1

HCID 591848352,4-Bis-benzyloxy-5-tert-butyl-6-chloro-pyrimidine収率 90%

実験手順

To a stirred anhydrous benzyl alcohol (80 ml), was added pieces of sodium metal (1.73 g, 75 mmol). After the reaction completed, the mixture was cooled in an ice bath and 5-tert-Butyl-2,4,6-trichloro-pyrimidine (9 g, 37.5 mmol) was added. After 1 hr., the mixture was stirred at room temperature for overnight and evaporated in vacuo. The residue was dissolved in ethyl acetate, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent, ether:hexanes (1:19)) to afford 13 g (90%) of a white solid. m.p. 96° C.; 1H NMR (200 MHz, CDCl3) δ 1.50 (9H, s), 5.37 (2H, s), 5.41 (2H, s), 7.34-7.46 (10H, m).