Methyl iodide → 3,4,4-Trimethoxyoxane

HRID 1436748Notes

Reaction equation

HRID 1436748 reaction equation
[CH3:1][O:2][C:3]1([O:10][CH3:11])[CH2:8][CH2:7][O:6][CH2:5][CH:4]1[OH:9].[H-].[Na+].[CH3:14]I>C1COCC1>[CH3:14][O:9][CH:4]1[C:3]([O:10][CH3:11])([O:2][CH3:1])[CH2:8][CH2:7][O:6][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 121909884,4-Dimethoxytetrahydro-2H-pyran-3-ol

Product 1

HCID 587845333,4,4-Trimethoxyoxane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4,4-dimethoxytetrahydro-2H-pyran-3-ol (6.00 g, 37.0 mmol) in THF (100 mL) at 0° C. was added sodium hydride (1.48 g, 37.0 mmol). After being stirred at 0° C. for 1 h, methyl iodide (4.61 mL, 74.0 mmol) was added dropwise. The reaction was allowed to warm up to ambient temperature and quenched using aqueous NH4Cl. The product was extracted with ether three times. The combined extracts were dried over Na2SO4 and concentrated. Purification by flash chromatography on silica gel (10% ether to 60% ether/hexanes) provided the desired product. 1H NMR (CDCl3) δ 4.05-3.95 (1H, m), 3.80-3.70 (1H, m), 3.60-3.50 (3H, m), 3.50 (3H, s), 3.30 (3H, s), 3.10 (3H, s), 2.00-1.70 (2H, m).

Workup

  1. temperatureto warm up to ambient temperature
  2. customquenched
  3. extractionThe product was extracted with ether three times
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (10% ether to 60% ether/hexanes)

Sources & evidence

ORD record
ord-48822e028e634eed9f15b45639449f02
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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