Sodium borohydride → HCID 13151493, compound

HRID 1648859Notes

Reaction equation

HRID 1648859 reaction equation
[Na].[CH:2]([CH:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:7][C:5]1=O)=[O:3].[BH4-].[Na+]>CO>[F:16][C:13]1[CH:12]=[CH:11][C:10]([CH:8]2[CH2:9][CH:4]([CH2:2][OH:3])[CH2:5][O:7]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5360545SodiumHCID 20481088alpha-Formyl-gamma-(4-fluorophenyl)-gamma-butyrolactone

Product 1

HCID 13151493HCID 13151493, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 200 g of sodium salt of α-formyl-γ-(4-fluorophenyl)-γ-butyrolactone in 1.5 liters of methanol is added slowly 70 g of sodium borohydride with stirring. The mixture is stirred at room temperature for 18 hours, and the methanol is then distilled off under reduced pressure. The residue is dissolved in 1 liter of water, and the solution is adjusted to pH 1 with concentrated sulfuric acid and heated under reflux for 1 hour. After cooling, the solution is adjusted to pH 11-12 with 40% aqueous sodium hydroxide solution, and stirred at 50° C. for 2 hours and then cooled. The reaction mixture is extracted twice with ethyl acetate. The combined extracts are washed with water and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is distilled to give 71 g of 2-(4-fluorophenyl)-4-(hydroxymethyl)tetrahydrofuran as colorless oil, boiling at 120°-126° C. (0.06 mmHg).

Workup

  1. stirringThe mixture is stirred at room temperature for 18 hours
  2. distillationthe methanol is then distilled off under reduced pressure
  3. dissolutionThe residue is dissolved in 1 liter of water
  4. temperatureheated
  5. temperatureunder reflux for 1 hour
  6. temperatureAfter cooling
  7. stirringstirred at 50° C. for 2 hours
  8. temperaturecooled
  9. extractionThe reaction mixture is extracted twice with ethyl acetate
  10. washThe combined extracts are washed with water
  11. dry with materialdried over magnesium sulfate
  12. distillationthe solvent is distilled off under reduced pressure
  13. distillationThe residue is distilled

Sources & evidence

ORD record
ord-1029819a3d9947b590c346767392a803
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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