Methyl iodide → (2-Methoxy-1-methoxymethyl-2-ethoxymethyl)-benzene

HRID 2361862

Reaction equation

HRID 2361862 reaction equation
[CH2:1]([O:8][CH:9]([CH2:12]O)CO)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CI.C1[CH2:22][O:21][CH2:20]C1.CN([CH:26]=[O:27])C>>[CH3:26][O:27][CH:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:12][CH2:20][O:21][CH3:22]

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2035672-(Phenylmethoxy)-1,3-propanediolHCID 21974620tetrahydrofuran N,N-dimethylformamide

Product 1

HCID 66890845(2-Methoxy-1-methoxymethyl-2-ethoxymethyl)-benzeneYield 97%

Procedure

To a solution of 2-benzyloxy-propane-1,3-diol (5.0 g, 27.4 mmol) in 5:1 THF-DMF (200 mL) at 0° C. was added NaH (1.5 g, 2.3 eq.) followed by methyl iodide (5.1 mL, 3.0 eq.). The resulting white slurry mixture was stirred at room temperature over weekend. The reaction mixture was quenched with sat. NH4Cl, extracted with EtOAc, dried over Na2SO4, filtered, concentrated and the product was purified by chromatography (50% EtOAc/hexanes) to give (2-methoxy-1-methoxymethyl-2-ethoxymethyl)-benzene (5.6 g, 97%).

Workup

  1. customThe reaction mixture was quenched with sat. NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe product was purified by chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4f690eec9d904eaa93e76943fee82bf4
Source dataset
uspto-grants-2014_04
Patent number
US08691814B2

Linked notes

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