Water → 8-Methoxy-8-(methoxymethyl)-1,4-dioxaspiro[4.5]decane

HRID 922119Notes

Reaction equation

HRID 922119 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([OH:14])[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1.[H-].[Na+].I[CH3:18].O>O1CCCC1>[CH3:18][O:14][C:4]1([CH2:3][O:2][CH3:1])[CH2:13][CH2:12][C:7]2([O:8][CH2:9][CH2:10][O:11]2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 712472648-(Methoxymethyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 712474008-Methoxy-8-(methoxymethyl)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.40 g (16.8 mmol) of the compound from Example 8A were dissolved in 170 ml of tetrahydrofuran, 1.01 g (25.2 mmol) of sodium hydride (60% in paraffin oil) were added and the mixture was stirred at room temperature for 0.5 hour. 3.58 g (25.2 mmol) of iodomethane were then added, and the reaction mixture was stirred at room temperature for two hours. 3.58 g (25.2 mmol) of iodomethane were then added, and the reaction mixture was stirred at room temperature for two hours. Water was added, the mixture was extracted repeatedly with ethyl acetate and the combined organic phases were dried over sodium sulphate, filtered and concentrated. This gave 3.35 g (92% of theory) of the title compound.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for two hours
  2. stirringthe reaction mixture was stirred at room temperature for two hours
  3. extractionthe mixture was extracted repeatedly with ethyl acetate
  4. dry with materialthe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-32958f47d1264cd592b62c6285ed0d1f
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

Loading…