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

HRID 930961Notes

Reaction equation

HRID 930961 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][C:6]1([OH:16])[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1.I[CH3:18].O>O1CCCC1>[CH3:18][O:16][C:6]1([CH2:5][O:4][CH3:3])[CH2:15][CH2:14][C:9]2([O:10][CH2:11][CH2:12][O:13]2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 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 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

To a mixture of 82.27 g sodium hydride (80%) in 2.1 L tetrahydrofuran was slowly added the solution of 208 g (1.03 mol) 8-(methoxymethyl)-1,4-dioxaspiro[4.5]decan-8-ol (prepared according to intermediate example 16f) in 1 L tetrahydrofuran under cooling. After 0.5 hours at 23° C. 143 mL iodomethane were added and the mixture was stirred at 23° C. overnight. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. After filtration and removal of the solvent 227.5 g (max. 100%) of the title compound were obtained that was used without further purification.

Workup

  1. temperatureunder cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and removal of the solvent 227.5 g (max. 100%) of the title compound
  6. customwere obtained
  7. customthat was used without further purification

Sources & evidence

ORD record
ord-0f474e6879d444bbbbf910f82f14d0bb
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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