Pyridine → HCID 53775323, compound

HRID 1584895Notes

Reaction equation

HRID 1584895 reaction equation
C(=O)(O)O.[C:5]1([CH:13]=[CH:12][CH:11]=[C:9]([OH:10])[C:7]=1[OH:8])[OH:6].[CH2:14]([C@H:16]1[O:18][CH2:17]1)Cl.N1C=CC=CC=1>C(OCC)(=O)C>[OH:6][C:5]1[C:7]2[O:8][C@@H:16]([CH2:17][OH:18])[CH2:14][O:10][C:9]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 149428(+)-EpichlorohydrinHCID 86754395HCID 86754395, compound

Product 1

HCID 53775323HCID 53775323, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of pyrogallol carbonate (8.2 g), (S)-epichlorohydrin (5.0 g) and dry pyridine (0.2 ml) in dry ethyl acetate (50 ml) was heated under reflux for 2 hours. The solvent was removed in vacuo, water (30 ml) was added, and the mixture heated under reflux for 30 minutes. A solution of potassium hydroxide (10 g) in water (20 ml) was added dropwise and the mixture heated under reflux under nitrogen for a further 30 minutes. The cooled mixture was diluted with water (100 ml), acidified with hydrochloric acid (5 M) then extracted with ethyl acetate (3×200 ml). The combined extracts were washed with water (2×100 ml) and dried over magnesium sulphate. The solvent was removed in vacuo and the residue purified by chromatography over silica eluting with a 1:1 mixture of ethyl acetate and petroleum ether (b.p. 60-80° C.) followed by neat ethyl acetate. Appropriate fractions were combined and the solvent removed in vacuo to give (S)-8-hydroxy-1,4-benzodioxan-2-ylmethanol (0.8 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed in vacuo, water (30 ml)
  4. additionwas added
  5. temperaturethe mixture heated
  6. temperatureunder reflux for 30 minutes
  7. additionA solution of potassium hydroxide (10 g) in water (20 ml) was added dropwise
  8. temperaturethe mixture heated
  9. temperatureunder reflux under nitrogen for a further 30 minutes
  10. additionThe cooled mixture was diluted with water (100 ml)
  11. extractionthen extracted with ethyl acetate (3×200 ml)
  12. washThe combined extracts were washed with water (2×100 ml)
  13. dry with materialdried over magnesium sulphate
  14. customThe solvent was removed in vacuo
  15. customthe residue purified by chromatography over silica eluting with a 1:1 mixture of ethyl acetate and petroleum ether (b.p. 60-80° C.)
  16. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-97c5e99490b548e8bd4a8266a628ecd8
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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