Tetrahydrofuran → N-[2-Fluoro-4-(1-hydroxypropyl)phenyl]methanesulfonamide

HRID 238939Notes

Reaction equation

HRID 238939 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12].[CH2:15]1COC[CH2:16]1>>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:9])[CH2:15][CH3:16])[CH:5]=[CH:4][C:3]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 71418417N-(2-Fluoro-4-formylphenyl)methanesulfonamide

Product 1

HCID 69528492N-[2-Fluoro-4-(1-hydroxypropyl)phenyl]methanesulfonamide

Conditions

Temperature
0 °C

Procedure

A cooled solution of N-(2-Fluoro-4-formylphenyl)methansulfonamide (20-3, 0.424 g, 2 mmol) in THF (20 mL) at 0° C. was treated with Grignard reagent (4 mmol) and stirred at 0° C. for 30 min. The reaction mixture was quenched with saturated ammonium chloride solution, diluted with water and extracted with EtOAc several times. The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:1) as eluant to N-[2-fluoro-4-(1-hydroxypropyl)phenyl]methanesulfonamide (20-4, LJO-337).

Workup

  1. customThe reaction mixture was quenched with saturated ammonium chloride solution
  2. additiondiluted with water
  3. extractionextracted with EtOAc several times
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-751127054a3348e3991bd0aaa284782d
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

Loading…