Methyl iodide → HCID 59203891, compound

HRID 2241831Notes

Reaction equation

HRID 2241831 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2[OH:16])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:17]I>>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2[O:16][CH3:17])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 68546191HCID 68546191, compound

Product 1

HCID 59203891HCID 59203891, compoundYield 43.5%

Procedure

2-Chloro-4-(cis-2-hydroxy-cyclopentyloxy)-benzonitrile (76 mg, 0.32 mmol) was added to a flame dried round bottom flask under nitrogen containing 2 mL of dry DMF and 8.5 mg of 60% sodium hydride as an oil dispersion (0.35 mmol). The reaction was stirred at room temperature for 1 h, after which time methyl iodide (54 mg, 0.38 mmol) was added. The mixture was stirred for 16 h, quenched by the dropwise addition of 5 mL of water, and extracted with ether (2×). The combined organic phases were washed with brine, dried (MgSO4), concentrated and purified by reverse phase HPLC (Shimadzu) to give 35 mg of the title compound. GC/MS: 251 (M/Z for C13H14ClNO2)—

Workup

  1. dry with materialdried round bottom flask under nitrogen containing 2 mL of dry DMF and 8.5 mg of 60% sodium hydride as an oil dispersion (0.35 mmol)
  2. stirringThe mixture was stirred for 16 h
  3. customquenched by the dropwise addition of 5 mL of water
  4. extractionextracted with ether (2×)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. custompurified by reverse phase HPLC (Shimadzu)

Sources & evidence

ORD record
ord-3712a62fbb4c408f8f77d5d81ec9fa54
Source dataset
uspto-grants-2010_03
Patent number
US07670613B2

Reaction notes

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