Potassium Carbonate → HCID 54448347, compound

HRID 1584884Notes

Reaction equation

HRID 1584884 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O[CH2:28][C@@H:29]2[O:31][CH2:30]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:16]([O:17][CH2:28][C@@H:29]2[O:31][CH2:30]2)=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 130703912-(Benzyloxy)-3-hydroxybenzaldehyde

Product 1

HCID 54448347HCID 54448347, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-benzyloxy-3-hydroxybenzaldehyde (60.0 g), (R)-glycidyl 4-toluenesulphonate (60.0 g) and potassium carbonate (74 g) in dry dimethylformamide (600 ml) was stirred and heated at 60° C. for 14 hours. After cooling the solvent was removed in vacuo , water (250 ml) added, and the mixture extracted with ether (2×200 ml), then ethyl acetate (2×400 ml). The combined extracts were washed with brine (2×500 ml) and dried over magnesium sulphate. The solvent was removed in vacuo and the residue purified by flash chromatography on silica, pre-adsorbing onto silica first by evaporation from a solution in dichloromethane, then eluting with a 3:1 mixture of petroleum ether (b.p. 40-60° C.) and ether. Appropriate fractions were combined and the solvent removed in vacuo to give (R)-2-benzyloxy-3-(2,3-epoxypropoxy)benzaldehyde (14.22 g). A further crop of product (33.37 g) was obtained by extraction of the silica employed in the chromatography with ether (6×500 ml), followed by concentration of the combined extracts to a volume of -500 ml and cooling overnight, filtering, then washing the precipitate with a 1:1 mixture of petroleum ether (b.p. 40-60° C.) and ether. The solvent was removed from the filtrate in vacuo and the residue purified by flash chromatography by the method described above, giving a third crop (9.68 g) of product. Combined yield of product 57.27 g.

Workup

  1. temperatureAfter cooling the solvent
  2. customwas removed in vacuo , water (250 ml)
  3. additionadded
  4. extractionthe mixture extracted with ether (2×200 ml)
  5. washThe combined extracts were washed with brine (2×500 ml)
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed in vacuo
  8. customthe residue purified by flash chromatography on silica
  9. custompre-adsorbing onto silica first by evaporation from a solution in dichloromethane
  10. washeluting with a 3:1 mixture of petroleum ether (b.p. 40-60° C.) and ether
  11. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1182e5dc2e47414c9853f8bd54e5faec
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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