Phosphorus oxychloride → HCID 15907971, compound

Reaction equation

P(Cl)(Cl)(Cl)=O.[C:6]([C@@:8]12[CH2:25][CH2:24][C:23]3[CH:22]=[C:21]([O:26][CH3:27])[CH:20]=[CH:19][C:18]=3[C@H:17]1[CH:16](O)[CH2:15][C@@:13]1([CH3:14])[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)#[N:7].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:6]([C@@:8]12[CH2:25][CH2:24][C:23]3[CH:22]=[C:21]([O:26][CH3:27])[CH:20]=[CH:19][C:18]=3[C:17]1=[CH:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)#[N:7]

Participants

Procedure

27.6 ml of phosphorus oxychloride was added in drops to a solution of 27.6 g of 4 in 275 ml of pyridine at a temperature of 0-5° C., and it was stirred for another 1.5 hours at this temperature. Then, the mixture was moved into a dropping funnel and added in drops to an ice-cooled, saturated sodium bicarbonate solution. Then, it was extracted with dichloromethane, the collected organic phases were washed with brine, dried on magnesium sulfate, and the solvent was removed in a vacuum. In this way, 23.5 g (89%) of almost colorless, foamy 5 was obtained, which was used without further purification in the next stage.