Sodium → [(2S)-8-Fluoro-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

HRID 1584875Notes

Reaction equation

HRID 1584875 reaction equation
[Na].C([O:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][CH2:13][C@@H:14]1[O:16][CH2:15]1)=O>CO>[F:11][C:10]1[C:5]2[O:4][C@@H:14]([CH2:15][OH:16])[CH2:13][O:12][C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 10774879(R)-2-(2,3-epoxypropoxy)-6-fluorophenyl formate

Product 1

HCID 54461939[(2S)-8-Fluoro-2,3-dihydro-1,4-benzodioxin-2-YL]methanolYield 67.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium metal (0.89 g) was dissolved in methanol (100 ml) and a solution of (R)-2-(2,3-epoxypropoxy)-6-fluorophenyl formate (6.56 g, prepared as described above) in methanol (100 ml) added dropwise. The mixture was stirred for one hour at ambient temperature then heated under reflux for two hours, allowed to stand for 3 days, and then heated under reflux for 4 hours. The solvent was removed in vacuo, water (100 ml) was added and the mixture extracted with ethyl acetate (4×100 ml). The combined extracts were washed with brine (100 ml), dried over magnesium sulphate and the solvent evaporated in vacuo to give crude (S)-8-fluoro-1,4-benzodioxan-2-ylmethanol (3.85 g) which was used without further purification.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for two hours
  3. waitto stand for 3 days
  4. temperatureheated
  5. temperatureunder reflux for 4 hours
  6. customThe solvent was removed in vacuo, water (100 ml)
  7. additionwas added
  8. extractionthe mixture extracted with ethyl acetate (4×100 ml)
  9. washThe combined extracts were washed with brine (100 ml)
  10. dry with materialdried over magnesium sulphate
  11. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-c9dddc622ad04f59900b173932d7f7bc
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

Loading…