Diethyl Ether → HCID 18516115, compound

HRID 1369631Notes

Reaction equation

HRID 1369631 reaction equation
[CH:1]([C:3]1[CH:8]=[N:7][CH:6]=[C:5]2[S:9][C:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:11][C:4]=12)=[O:2].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1.C(OCC)C>C1COCC1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:1]([OH:2])[C:3]2[CH:8]=[N:7][CH:6]=[C:5]3[S:9][C:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:11][C:4]=23)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 18516175HCID 18516175, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 18516115HCID 18516115, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 237E (0.25 g, 0.95 mmol) in anhydrous THF (5 mL) at −5° C. was slowly added a 1 M solution of p-chlorophenylmagnesium bromide in diethyl ether (2.85 mL, 2.85 mmol). The reaction was quench after 10 minutes with dropwise addition of water (1 mL) and partitioned between dichloromethane (25 mL) and 50% sat. aq NaHCO3 (50 mL). The aqueous phase was extracted with dichloromethane (25 mL) and the organic extracts combined, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel using EtOAc/hexane as eluent to provide the title compound as a foam, which was crushed and dried in a desiccator to yield a powder (0.36 g, 100%).

Workup

  1. customThe reaction was quench after 10 minutes with dropwise addition of water (1 mL)
  2. custompartitioned between dichloromethane (25 mL) and 50% sat. aq NaHCO3 (50 mL)
  3. extractionThe aqueous phase was extracted with dichloromethane (25 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1c50950d74e44cabbb94855efb27e8f2
Source dataset
uspto-grants-2003_06
Patent number
US06579882B2

Reaction notes

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