Methyl iodide → HCID 18932679, compound

HRID 1598424Notes

Reaction equation

HRID 1598424 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]2[C:6]=1[CH2:7][CH:8]([CH2:17][OH:18])[O:9][CH2:10]2.I[CH3:20]>O1CCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>[CH3:3][O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]2[C:6]=1[CH2:7][CH:8]([CH2:17][O:18][CH3:20])[O:9][CH2:10]2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 18932683HCID 18932683, compound

Product 1

HCID 18932679HCID 18932679, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 10796Cesium carbonateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (70 mg of 60% in oil; 1.78 mmol) in tetrahydrofuran (3 ml) was added a solution of 5,8-dimethoxy-3-hydroxymethyl-isochroman (330 mg; 1.48 mmol) in 7 ml of tetrahydrofuran. The resulting mixture was stirred at room temperature until H2 evolution ceased (~15 minutes) and iodomethane (500 μl; 5 eq) was added. The mixture was then stirred at room temperature for 30 minutes. Since the reaction was not complete, another equivalent of sodium hydride was added along with 20 mg of cesium carbonate. The mixture was stirred for 15 minutes and was quenched with saturated ammonium chloride solution and extracted with dichloromethane. The combined organic layers were washed with brine and dried over MgSO4. The crude was purified by column chromatography on silica gel using 25% ethyl acetate in hexane to afford the title compound (301 mg; 86%):

Workup

  1. additionwas added
  2. stirringThe mixture was then stirred at room temperature for 30 minutes
  3. stirringThe mixture was stirred for 15 minutes
  4. customwas quenched with saturated ammonium chloride solution
  5. extractionextracted with dichloromethane
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. customThe crude was purified by column chromatography on silica gel using 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bf9476bcaaa341f2b9f260692c1f15d4
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

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