Water → 8-Cyclohexyl-8-methoxy-1,4-dioxaspiro[4.5]decane

HRID 1816763Notes

Reaction equation

HRID 1816763 reaction equation
[CH:1]1([C:7]2([OH:17])[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I[CH3:19].[H-].[Na+].O>CN(C)C=O.ClCCl>[CH:1]1([C:7]2([O:17][CH3:19])[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 224947648-Cyclohexyl-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 224947668-Cyclohexyl-8-methoxy-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-cyclohexyl-1,4-dioxaspiro[4.5]decan-8-ol (1.143 g) and iodomethane (0.59 ml) in N,N-dimethylformamide (11 ml) was added sodium hydride (60% dispersion in mineral oil) (342 mg) at 0° C. The solution was stirred for 9 hours at 0° C., during which period additional iodomethane (0.59 ml) and sodium hydride (60% dispersion in mineral oil) (344 mg) was added to the mixture. The reaction mixture was added to a mixture of water and dichloromethane. The organic layer was washed with water. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate elution) to give 8-cyclohexyl-8-methoxy-1,4-dioxaspiro[4.5]decane (1.201 g).

Workup

  1. additionwas added to the mixture
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate elution)

Sources & evidence

ORD record
ord-b9d5e51fd8ea4585b578156732c5a7d9
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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