Dimethylformamide → (+/-)-(E)-1-(2-Methoxy-4-(2-phenylethenyl)phenoxy)-5-(3-pyridyl)-2-pentanol

HRID 1600990Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[O:18][CH3:19].C1(C)C=CC(S(O[CH2:30][CH2:31][CH:32](O)[CH2:33][CH2:34][C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)(=O)=O)=CC=1.CN(C)C=[O:46]>>[CH3:19][O:18][C:5]1[CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:8]=[CH:9][C:4]=1[O:3][CH2:30][CH:31]([OH:46])[CH2:32][CH2:33][CH2:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 7198144-Hydroxy-3-methoxystilbene

HCID 21830649HCID 21830649, compound

Product 1

HCID 21830709(+/-)-(E)-1-(2-Methoxy-4-(2-phenylethenyl)phenoxy)-5-(3-pyridyl)-2-pentanol

Procedure

Prepared according to the method described in Example 96d) from sodium hydride (60% dispersion in mineral oil, 55 mg), trans-4-hydroxy-3-methoxystilbene (0.314 g) and (±)-3-hydroxy-5-(3-pyridyl)-1-pentyl para-toluenesulfonate (310 mg) in anhydrous dimethylformamide (6 ml). The crude product was purified by column chromatography over silica eluting with methanol:dichloromethane (1:19) to give the title compound (0.197 g) as a solid which was recrystallised from ethyl acetate:hexane.

Workup

customPrepared
customThe crude product was purified by column chromatography over silica eluting with methanol:dichloromethane (1:19)

Sources & evidence

ORD record: ord-3f04681ee4b041a09b2b0de5418945ab
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977105

Reaction notes

Loading…