Borane → (3-Methanesulfonylphenyl)methanol

HRID 1642619Notes

Reaction equation

HRID 1642619 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])(=[O:4])=[O:3].B.B(F)(F)F.CCOCC>C1COCC1>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[CH2:8][OH:9])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6331BoraneHCID 8000Boron trifluoride etherateHCID 2203803-Methanesulfonylbenzoic acid

Product 1

HCID 23549738(3-Methanesulfonylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(methylsulfonyl)benzoic acid (1.2 g, 6.0 mmol) in THF (30 mL) at 0° C., is added equimolar amounts of borane (6.0 mL of a 1.0 M solution in THF) and boron trifluoride diethyl etherate (0.8 mL, 6.0 mmol). The reaction is allowed to warm to ambient temperature overnight, and then quenched by pouring into a mixture of ice and solid NaHCO3. Following extraction with EtOAc, the organic layer is washed with brine and dried over Na2SO4. Removal of solvent affords the product as a colorless oil: MS (M+NH4)+=204.

Workup

  1. customquenched
  2. additionby pouring into a mixture of ice and solid NaHCO3
  3. extractionextraction with EtOAc
  4. washthe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-daaa337f742940e68ed722cc107bfa3a
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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