Water → HCID 19373306, compound

HRID 129323Notes

Reaction equation

HRID 129323 reaction equation
[OH:1][CH2:2][C:3]1([CH2:11][OH:12])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1.[H-].[Na+].[CH2:15](I)[CH3:16].O>CN(C)C=O>[CH3:10][C:6]1([CH3:9])[O:5][CH2:4][C:3]([CH2:11][O:12][CH2:15][CH3:16])([CH2:2][OH:1])[CH2:8][O:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 373708NSC650609

Product 1

HCID 19373306HCID 19373306, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 5,5-di-(hydroxymethyl)-2,2-dimethyl-1,3dioxane (5.09) (Bellstein 19, II, 93) in dry dimethylformamide (50 ml) under nitrogen, at 20°, was added sodium hydride (0.689g, 80% dispersion in oil). The mixture was stirred at 80° for 2 hours and cooled. Ethyl iodide (4.49g) in dry dimethylformamide (40 ml) was added and the mixture was heated at 110° for 3 hours. The mixture was cooled and poured into water. The aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with brine, dried over anhydrous magnesium sulphate and evaporated in vacuo. 2,2-Dimethyl-5-ethoxymethyl-5- hydroxymethyl-1,3-dioxane was obtained as a pale yellow oil (1.2 g) and was used without further purification.

Workup

  1. temperaturecooled
  2. temperaturethe mixture was heated at 110° for 3 hours
  3. temperatureThe mixture was cooled
  4. extractionThe aqueous mixture was extracted with diethyl ether
  5. washThe ethereal extracts were washed with brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-75883112f17b4ad99dff58ff1224eedc
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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