Potassium Carbonate → (3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-ol

HRID 1505578

Reaction equation

HRID 1505578 reaction equation
C([O:4][C@@H:5]1[C@H:12]2[C@H:8]([O:9][CH2:10][CH2:11]2)[O:7][CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.ClCCl>[O:7]1[C@H:8]2[O:9][CH2:10][CH2:11][C@H:12]2[C@@H:5]([OH:4])[CH2:6]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59959307(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl acetate

Product 1

HCID 9942150(3R,3aS,6aR)-hexahydrofuro(2,3-b)furan-3-olYield 99.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl acetate (II, 14.0 g) was dissolved in methanol (42 mL). Potassium carbonate (0.34 g) was added and stirred at 25-35° C. for 6-8 hours. Methanol Was distilled out completely under vacuum, to the distillate methylenedichloride (28 mL) was added, stirred the mass for 30 minutes and again distilled the solvent to get residue. Dissolved the residue in dichloromethane (56 mL), the resultant solution was treated with carbon and the solvent was completely distilled out get title compound I (yield 10.5 g).

Workup

  1. distillationMethanol Was distilled out completely under vacuum, to the distillate methylenedichloride (28 mL)
  2. additionwas added
  3. stirringstirred the mass for 30 minutes
  4. distillationagain distilled the solvent
  5. customto get residue
  6. distillationthe solvent was completely distilled out

Sources & evidence

ORD record
ord-55ddae41e48d4439bdad97b451074da2
Source dataset
uspto-grants-2015_12
Patent number
US09216990B2

Linked notes

Loading…