Methyl iodide → HCID 66593061, compound

HRID 491037Notes

Reaction equation

HRID 491037 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH2:24][CH2:25][OH:26])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:30]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH2:24][CH2:25][O:26][CH3:30])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57675743HCID 57675743, compound

Product 1

HCID 66593061HCID 66593061, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[1-(4-Benzyloxyphenyl)-1H-indol-2-yl]ethanol (0.675 mmol) was dissolved in tetrahydrofuran (5 mL) under N2, and sodium hydride (81 mg, 60% dispersion in mineral oil, 2.03 mmol) was added. The reaction was heated to reflux, at which time iodomethane (0.42 mL, 6.75 mmol) was added. The reaction was stirred at reflux for 3 hours, then carefully quenched with water. The mixture was extracted with ethyl acetate, dried over MgSO4, and concentrated. The residue was purified by SiO2 chromatography (5-20% ethyl acetate/hexanes) to give the desired product, 0.14 g. LC-MS (C24H23NO2 calc'd 357) m/z 358 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. additionwas added
  3. temperatureat reflux for 3 hours
  4. customcarefully quenched with water
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by SiO2 chromatography (5-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-aa94e758951e4338ac3b8b66119759f3
Source dataset
uspto-grants-2009_05
Patent number
US07528262B2

Reaction notes

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