1,2-Dimethoxyethane → HCID 54138531, compound

Reaction equation

[H-].[Na+].[N:3]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[N:6]=[CH:5][CH:4]=1.C[C:18]#[C:19][C:20]([O-:22])=[O:21].[CH2:23](COC)OC>>[C:20]([CH:19]=[CH:18][N:15]1[C:16]2[N:3]=[CH:4][CH:5]=[N:6][C:7]=2[S:8][C:9]2[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=2)([O:22][CH3:23])=[O:21]

Participants

Reactant 4

HCID 80711,2-Dimethoxyethane

HCID 24758Sodium hydride

HCID 6994510HCID 6994510, compound

HCID 12351784HCID 12351784, compound

Product 1

HCID 54138531HCID 54138531, compound

Procedure

To a suspension of sodium hydride (0.1 g, 4.2 mmoles) in dimethoxyethane (10 ml) was added 1,4-diazaphenothiazine (200 mg, 1 mmole). After stirring for 30 minutes a deep red solution of the anion was obtained and this was treated with methylpropiolate (85 μl, 1.0 mmole). Stirring was maintained for 30 minutes. The mixture was evaporated to dryness and the residue was purified by chromatography. Elution with 40% EtOAc/hexane gave the desired product as on orange solid, m.p. 165°-169°. NMR analysis showed the product to be a mixture of trans and cis isomers in a ratio of 4 to 1.