Methyl iodide → 8-[(Methyloxy)methyl]-1,4-dioxaspiro[4.5]decane

HRID 420770Notes

Reaction equation

HRID 420770 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:13]I.[H-].[Na+]>O1CCCC1>[CH3:13][O:12][CH2:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 100808381,4-Dioxaspiro[4.5]decan-8-ylmethanol

Product 1

HCID 575773188-[(Methyloxy)methyl]-1,4-dioxaspiro[4.5]decaneYield 780%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,4-Dioxaspiro[4.5]decane-8-methanol (2 g, 1 mmol) (commercial available or prepared as in Bioorganic & Medicinal Chemistry, 13(23), 6309-6323; 2005) is methylated using MeI (1.81 mL, 29 mmol) and NaH (0.813 g, 20 mmol) in tetrahydrofuran to obtain after 2 hours of stirring at room temperature 1.4 g (7.8 mmol) of the desired compound. MS (m/e): 187.3 (M+H+).

Workup

  1. customto obtain after 2 hours

Sources & evidence

ORD record
ord-011bd74e02684efd94b8e06139178830
Source dataset
uspto-grants-2012_01
Patent number
US08097637B2

Reaction notes

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