Methyl iodide → HCID 601314, compound

HRID 1089848Notes

Reaction equation

HRID 1089848 reaction equation
[C:1]1([CH2:14][OH:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:16]([Li])CCC.IC.C(OCC)(=O)C>C1COCC1.CCCCCC>[CH3:16][O:15][CH2:14][C:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 523071-FluorenemethanolHCID 178418339Butyllithium

Product 1

HCID 601314HCID 601314, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 1-fluorenemethanol (5.0 g, 25.6 mmol) in 50 mL of THF was charged with butyl lithium solution (11.0 mL, 26.0 mmol) at -78° C. After 15 min of stirring iodomethane (25.1 g, 176.1 mmol) was introduced. The reaction mixture was stirrer for 3 days at room temperature. The reaction was monitored by TLC (silica, 25% ethyl acetate in hexane). As soon as no more starting material was detected the reaction was quenched with water (30 mL). The organic layer was separated, washed with water, brine, dried over magnesium sulfate and evaporated. A short path chromatography of the residual oil (silica, 5% ethyl acetate in hexane) afforded 4.5 g (70.0%) of 1-methoxymethylfluorene.

Workup

  1. customfor 3 days
  2. customat room temperature
  3. customwas quenched with water (30 mL)
  4. customThe organic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-3d5df40f02204628be0270a87dc5d844
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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