Dimethylformamide → 5-Benzyloxy-2,2-dimethyl-1,3-dioxane

HRID 1645542

Reaction equation

HRID 1645542 reaction equation
CN(C)C=O.[CH3:6][C:7]1([CH3:14])[O:12][CH2:11][CH:10]([OH:13])[CH2:9][O:8]1.[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:17]([O:13][CH:10]1[CH2:11][O:12][C:7]([CH3:14])([CH3:6])[O:8][CH2:9]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 110298842,2-Dimethyl-1,3-dioxan-5-ol

Product 1

HCID 203648895-Benzyloxy-2,2-dimethyl-1,3-dioxaneYield 54.5%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

To a N,N-dimethylformamide (200 ml) solution of the 2,2-dimethyl-1,3-dioxan-5-ol (7.1 g, 0.054 mol) obtained in the step (9a), sodium hydride, in oil (2.81 g, 0.064 mol as the content was regarded as 55%) was added at 0° C. and stirred. After benzyl bromide (12.9 ml, 0.108 mol) and tetrabutylammonium iodide (220 mg, 0.001 mol) were added at the same temperature to the mixture, the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate three times. Organic layers were combined, washed five times with water and once with a saturated saline solution, dried over anhydrous sodium sulfate, and filtered. After NH silica gel was added, the resultant mixture was concentrated and purified by silica gel column chromatography (elution solvent: heptane, heptane/ethyl acetate=9/1, 4/1, ethyl acetate) to obtain the title compound (6.5 g, 54.5%) as a colorless oil.

Workup

  1. additionwas added at 0° C.
  2. stirringthe mixture was stirred at room temperature for 1.5 hours
  3. extractionwas then extracted with ethyl acetate three times
  4. washwashed five times with water
  5. dry with materialonce with a saturated saline solution, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. additionAfter NH silica gel was added
  8. concentrationthe resultant mixture was concentrated
  9. custompurified by silica gel column chromatography (elution solvent: heptane, heptane/ethyl acetate=9/1, 4/1, ethyl acetate)

Sources & evidence

ORD record
ord-3ed6ca2a0d234cbb978cc9a7de249aba
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Linked notes

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