Dimethylformamide → HCID 21830733, compound

HRID 1600987Notes

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][CH:5]=1.C1(C)C=CC(S(O[CH2:28][CH2:29][CH:30](O)[CH2:31][CH2:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)(=O)=O)=CC=1.CN(C)C=[O:44]>>[C:12]1(/[CH:11]=[CH:10]/[C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:28][CH:29]([OH:44])[CH2:30][CH2:31][CH2:32][C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)=[CH:9][CH:8]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 5284650trans-4-Hydroxystilbene

HCID 21830649HCID 21830649, compound

Product 1

HCID 21830733HCID 21830733, compound

Procedure

Prepared according to the method described in Example 96d) from sodium hydride (60% dispersion in mineral oil, 0.045 g), trans-4-hydroxystilbene (0.219 g) and (±)-3-hydroxy-5-(3-pyridyl)-1-pentyl para-toluenesulfonate (0.250 g) in anhydrous dimethylformamide (5 ml). The crude product was purified by column chromatography over silica eluting with methanol:dichloromethane (1:19) to give the title compound (0.167 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-36eed73b05614b5990d3a1ffbf140e55
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977105

Reaction notes

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