1,6-Di-O-(p-toluenesulphonyl)-2,5-anhydro-D-mannitol → (2R,3S,4S,5R)-2,5-dimethyltetrahydrofuran-3,4-diol

HRID 459423Notes

Reaction equation

HRID 459423 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1(C)C=CC(S(O[CH2:17][C@H:18]2[O:24][C@H:23]([CH2:25]OS(C3C=CC(C)=CC=3)(=O)=O)[C@@H:21]([OH:22])[C@@H:19]2[OH:20])(=O)=O)=CC=1.[H][H]>C1COCC1>[CH3:25][C@H:23]1[O:24][C@H:18]([CH3:17])[C@@H:19]([OH:20])[C@@H:21]1[OH:22]

Participants

5

Reactant 3

HCID 140769161,6-Di-O-(p-toluenesulphonyl)-2,5-anhydro-D-mannitolHCID 21226445Aluminium lithium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 11105400(2R,3S,4S,5R)-2,5-dimethyltetrahydrofuran-3,4-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.86 g (22.66 mmol) of LiAlH4 was added to a solution of 3.60 g (7.63 mmol) of B3 in 20 ml of anhydrous THF and stirred at reflux for 2 hours. After cooling, Arberlite® IR-120(plus) was added and stirring was continued until hydrogen evolution had ended. The mixture was filtered through Celite® and the solvent was subsequently removed under reduced pressure. The crude product was purified by means of column chromatography (CH2Cl2/MeOH=12:1). Yield: 0.84 g (84% of theory).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureAfter cooling
  3. additionArberlite® IR-120(plus) was added
  4. stirringstirring
  5. filtrationThe mixture was filtered through Celite®
  6. customthe solvent was subsequently removed under reduced pressure
  7. customThe crude product was purified by means of column chromatography (CH2Cl2/MeOH=12:1)

Sources & evidence

ORD record
ord-b11d81f910544e3dbcb02dbf9a8f8ec2
Source dataset
uspto-grants-2007_03
Patent number
US07193092B2

Reaction notes

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