1,2-Dimethoxyethane → HCID 54138531, compound

HRID 979981Notes

Reaction equation

HRID 979981 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

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 6994510HCID 6994510, compoundHCID 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.

Workup

  1. customwas obtained
  2. stirringStirring
  3. temperaturewas maintained for 30 minutes
  4. customThe mixture was evaporated to dryness
  5. customthe residue was purified by chromatography
  6. washElution with 40% EtOAc/hexane

Sources & evidence

ORD record
ord-b000da798df54451ad7d1f056ecf7daf
Source dataset
uspto-grants-1987_01
Patent number
US04634766

Reaction notes

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