Sodium borohydride → 1,4-Di-[(methanesulfonyl)oxy]-2-(hydroxymethyl)benzene

HRID 412163Notes

Reaction equation

HRID 412163 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:13]=[CH:12][C:11]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][C:7]=1[CH:8]=[O:9])(=[O:4])=[O:3].[BH4-].[Na+]>C1COCC1.C(O)C>[CH3:1][S:2]([O:5][C:6]1[CH:13]=[CH:12][C:11]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][C:7]=1[CH2:8][OH:9])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 185361862.5-Di-[(methanesulfonyl)oxy]benzaldehyde

Product 1

HCID 185360451,4-Di-[(methanesulfonyl)oxy]-2-(hydroxymethyl)benzene

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of the product from Step A (17.13 g, 58.2 mmol) in 150 mL of 2:1 THF/ethanol at 0° C. was added sodium borohydride (2.27 g, 60.0 mmol). After 30 minutes, the reaction was carefully quenched by the addition oc saturated NH4Cl solution, then partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated as a yellow oil which was used without further purification.

Workup

  1. customthe reaction was carefully quenched by the addition oc saturated NH4Cl solution
  2. custompartitioned between EtOAc and saturated NaHCO3 solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was isolated as a yellow oil which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-af8b38658e2845c38b40455500b14b75
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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