Tetrahydrofuran → [4-(Phenylsulfonyl)phenyl]methanol

HRID 1644698Notes

Reaction equation

HRID 1644698 reaction equation
[BH4-].[Na+].[C:3]1([S:9]([C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O1CCCC1>C(OCC)(=O)C>[C:3]1([S:9]([C:12]2[CH:13]=[CH:14][C:15]([CH2:16][OH:17])=[CH:18][CH:19]=2)(=[O:10])=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 144174774-(Benzenesulfonyl)benzaldehyde

Product 1

HCID 12801750[4-(Phenylsulfonyl)phenyl]methanolYield 61.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (777 mg, 20.5 mmol) was added slowly in portions to a 0° C. solution of 4-(benzenesulfonyl)-benzaldehyde (4.29 g, 18.6 mmol) and tetrahydrofuran (60 mL). The reaction mixture was allowed to warm to room temperature, then stirred at room temperature for 4 hours. The reaction mixture was then cooled over an ice-water bath, diluted with ethyl acetate (80 mL), then carefully quenched with a saturated aqueous solution of ammonium chloride (10 mL). The mixture was washed with water (80 mL), then the organic phase was dried over MgSO4, filtered, and concentrated to afford 2.83 g (61%) of (4-benzenesulfonyl-phenyl)-methanol as a white solid. This product was used in subsequent steps without further purification.

Workup

  1. temperatureThe reaction mixture was then cooled over an ice-water bath
  2. customcarefully quenched with a saturated aqueous solution of ammonium chloride (10 mL)
  3. washThe mixture was washed with water (80 mL)
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bced6965b97f4320b56cfae3e32fc1f8
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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