Tetrahydrofuran → HCID 318403, compound

HRID 572572Notes

Reaction equation

HRID 572572 reaction equation
C([Mg]Cl)(C)C.I[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1.S([O-])(O)(=O)=[O:16].[K+].C1[CH2:25][O:24][CH2:23][CH2:22]1>>[CH3:25][O:24][CH2:23][C:22]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:16]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 764674-IodobenzonitrileHCID 516920Potassium bisulfateHCID 178418918HCID 178418918, compound

Product 1

HCID 318403HCID 318403, compound

Procedure

Iso-propyl magnesium chloride (2 M solution in THF; 3.0 mL; 6.0 mmol) was added to an ice-cooled solution of 4-iodobenzonitrile (1.2 g, 5.0 mmol) in anhydrous THF (10 mL). This solution was stirred at this temperature for 10 minutes and then added dropwise to a cooled (−78° C.) solution of N-2-dimethoxy-N-methylacetamide (0.998 g, 7.50 mmol) in anhydrous THF (5 mL). The reaction mixture was stirred at this temperature for 1 hour and then stirred at RT for 1 hour. The reaction mixture was then treated with 10% aqueous potassium hydrogen sulfate solution and extracted with DCM. The organic phase was passed through a hydrophobic frit and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with iso-hexane/EtOAc (3:2) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.06-8.04 (m, 2H), 7.80-7.77 (m, 2H), 4.67 (s, 2H), 3.50 (s, 3H).

Workup

  1. additionadded dropwise to
  2. stirringThe reaction mixture was stirred at this temperature for 1 hour
  3. stirringstirred at RT for 1 hour
  4. extractionextracted with DCM
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with iso-hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-a02f99ef32fc49a6825dd92306c8e6a9
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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