Hydrochloric Acid → HCID 18650779, compound

HRID 1614571Notes

Reaction equation

HRID 1614571 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][CH:22]=1)[O:8][C:9]1[C:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:12]=[CH:11][N:10]=1.[CH:23]([O:25][CH3:26])=O.Cl>CN(C=O)C.O>[OH:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][CH:22]=1)[O:8][C:9]1[C:14](/[C:15](=[CH:23]\[O:25][CH3:26])/[C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 19771879HCID 19771879, compound

Product 1

HCID 18650779HCID 18650779, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (1.056 g, 50% dispersion in oil, pre-washed with petroleum ether) in dry DMF (15 ml) at 0°-5° C. was added dropwise over 5 minutes a solution containing methyl 2-(3-hydroxymethylphenoxy)pyridin-3-ylacetate (2.0 g) and methyl formate (9 ml) in DMF (effervescence). After the addition was complete, the reaction mixture was allowed to warm to room temperature. After stirring for a further 3 hours, the reaction mixture was carefully poured into water, neutralised with 2N hydrochloric acid and then extracted thoroughly with ether (× 6). The combined ether layers were dried, filtered and evaporated to afford a crude residue which was used without further purification. The residue was dissolved in DMF (10 ml) and then treated with potassium carbonate (0.60 g) and dimethyl sulphate (0.64 g). Standard work-up and chromatography on silica gel (eluent petroleum ether-ether, 1:1) afforded (E)-methyl 2-[2-(3hydroxymethylphenoxy)pyridin-3-yl]-3-methoxypropenoate (0.35 g, 15%); mass spectrum m/e 315 (M+).

Workup

  1. additionwas added dropwise over 5 minutes a solution
  2. additionAfter the addition
  3. extractionextracted thoroughly with ether (× 6)
  4. dry with materialThe combined ether layers were dried
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a crude residue which
  8. customwas used without further purification
  9. dissolutionThe residue was dissolved in DMF (10 ml)
  10. additiontreated with potassium carbonate (0.60 g) and dimethyl sulphate (0.64 g)

Sources & evidence

ORD record
ord-be8e8a35b7e746e785b7594650d9029f
Source dataset
uspto-grants-1993_03
Patent number
US05198444

Reaction notes

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