Water → (+/-)2-Hydroxy-5-(p-Toluenesulfonyloxymethyl)-Tetrahydrofuran

HRID 636876Notes

Reaction equation

HRID 636876 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][CH:12]2[O:16][C:15](=[O:17])[CH2:14][CH2:13]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C.O>C1(C)C=CC=CC=1>[OH:17][CH:15]1[CH2:14][CH2:13][CH:12]([CH2:11][O:10][S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:18])=[CH:6][CH:5]=2)(=[O:9])=[O:8])[O:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 4609541(5-Oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 21255848(+/-)2-Hydroxy-5-(p-Toluenesulfonyloxymethyl)-Tetrahydrofuran

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of (±)-dihydro-5-(p-toluensulfonyloxymethyl)-2(3H)-furanone (example 57) (5.20 g, 19.26 mmol) in anhydrous toluene (125 mL) at −78° C. was added DIBAL (1.5 M in toluene, 13.5 mL, 20.22 mmol) dropwise. The solution was allowed to stir at −78° C. for 2 h. water was then added to the mixture and the reaction mixture was brought to rt. The mixture was filtered through a CELITE diatomaceous earth and the organic layer was collected, dried (MgSO4) and concentrated to give the title compound as a 1:1 mixture of cis and trans isomers (4.2 g, 80%).

Workup

  1. additionwas then added to the mixture
  2. customwas brought to rt
  3. filtrationThe mixture was filtered through a CELITE diatomaceous earth
  4. customthe organic layer was collected
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-49b82164d2a64d1da9648ce6ab6901a4
Source dataset
uspto-grants-2001_02
Patent number
US06194576B1

Reaction notes

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