Potassium Carbonate → HCID 10655958, compound

HRID 1584880Notes

Reaction equation

HRID 1584880 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].C1(C)C=CC(S(O[CH2:22][C@@H:23]2[O:25][CH2:24]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:25]1[CH2:24][C@@H:23]1[CH2:22][O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 154187Glycidyl tosylate, (R)-

Product 1

HCID 10655958HCID 10655958, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-hydroxy-5-methoxybenzaldehyde (6.65 g), (R)-glycidyl 4-toluenesulphonate (10.0 g) and potassium carbonate (6.1 g) in dry dimethylformamide (100 ml) was stirred and heated at 60° C. for five hours. The solvent was removed in vacuo, water was added to the residue and the mixture extracted with ether (2×200 ml). The combined extracts were washed with water and dried over magnesium sulphate. The solvent was evaporated and the residue purified by flash chromatography over silica eluting with a 2:1 mixture of ether and petroleum ether (b.p. 40-60° C.). Appropriate fractions were combined and the solvent evaporated to give (R)-2-(2,3-epoxypropoxy)-5-methoxybenzaldehyde (7.25 g) as a clear oil.

Workup

  1. customThe solvent was removed in vacuo, water
  2. additionwas added to the residue
  3. extractionthe mixture extracted with ether (2×200 ml)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customThe solvent was evaporated
  7. customthe residue purified by flash chromatography over silica eluting with a 2:1 mixture of ether and petroleum ether (b.p. 40-60° C.)
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-562c6f17358341b88169c29c2d5ed504
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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