Acetonitrile → HCID 54196047, 화합물

반응식

Cl[C:2]1[N:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[OH:9][C:10]1[CH:22]=[CH:21][C:13]([O:14][CH:15](O)[CH:16]=[CH:17]CC)=[CH:12][CH:11]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+].[C:29](#N)C>>[I:8][C:5]1[CH:4]=[N:3][C:2]([O:9][C:10]2[CH:11]=[CH:12][C:13]([O:14][CH:15]([CH3:29])[CH:16]=[CH:17][CH2:23][OH:26])=[CH:21][CH:22]=2)=[N:7][CH:6]=1

참가 물질

반응물 4

HCID 6342Acetonitrile

HCID 11430Potassium Carbonate

HCID 17142232-Chloro-5-iodopyrimidine

HCID 86742038HCID 86742038, 화합물

생성물 1

HCID 54196047HCID 54196047, 화합물

실험 절차

A mixture of 1.68 g (7 mmol) of 2-chloro-5-iodopyrimidine, 1.55 g (8 mmol) of (E)-4-(4-hydroxy-phenoxy-2-penten-1-ol, 1.24 g (9 mmol) of powdered, anhydrous potassium carbonate and 35 ml of dry acetonitrile was stirred under nitrogen at reflux for a period of 3 hours. The mixture was cooled and filtered, and the filtered solid was thoroughly washed with ether. The filtrates were combined and evaporated to dryness, and the residue partitioned between ether and 1 percent aqueous sodium hydroxide. The aqueous layer was separated and again extracted with ether. The combined organic layers were washed twice with water, dried over MgSO4 and evaporated to dryness. The residual oil was purified by preparative scale HPLC, and then dried in a Kugelrohr apparatus at 55° C. and 0.1 mm Hg for 1 hour. This left 2.75 g (quantitative) of the desired pentenol as a pale yellow, viscous gum.