Water → 8-Methoxy-8-phenyl-1,4-dioxaspiro[4.5]decane

HRID 1816348Notes

Reaction equation

HRID 1816348 reaction equation
[C: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)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[CH3:19].[H-].[Na+].O>CN(C)C=O.CCOCC>[CH3:19][O:17][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 149775528-Phenyl-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 224929828-Methoxy-8-phenyl-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8-phenyl-1,4-dioxaspiro[4.5]decan-8-ol (5.76 g) and iodomethane (4.59 ml) in N,N-dimethylformamide (58 ml) was added sodium hydride (60% dispersion in mineral oil) (1.97 g) at 0° C. The solution was stirred for 2 hours at 0° C. and at room temperature for 7.5 hours. The reaction mixture was added to a mixture of water and ether. The organic layer was washed with brine 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 (5:1 hexane-ethyl acetate elution) to give 8-methoxy-8-phenyl-1,4-dioxaspiro[4.5]decane (5.968 g).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (5:1 hexane-ethyl acetate elution)

Sources & evidence

ORD record
ord-182e411140474c0b8866c5e6f4d12c8e
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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