Methyl iodide → 8-Benzyl-8-methoxy-1,4-dioxaspiro[4.5]decane

HRID 900080Notes

Reaction equation

HRID 900080 reaction equation
[CH2:1]([C:8]1([OH:18])[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:22]>C1COCC1>[CH2:1]([C:8]1([O:18][CH3:22])[CH2:17][CH2:16][C:11]2([O:12][CH2:13][CH2:14][O:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 221798308-Benzyl-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 221798428-Benzyl-8-methoxy-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 11A (8.08 g, 32.5 mmol) in THF (150 mL) at room temperature was treated with 60% NaH in mineral oil (3.2 g, 80 mmol), stirred for 1 hour, treated with iodomethane (5 mL, 80 mmol), stirred overnight, quenched with saturated NH4Cl, and extracted with ethyl acetate (3×200 mL). The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product. MS (CI) m/e 280.2 (M+18)+.

Workup

  1. stirringstirred overnight
  2. customquenched with saturated NH4Cl
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b18e594751834ba8b9b806f8b0c1f2ff
Source dataset
uspto-grants-2008_04
Patent number
US07358251B2

Reaction notes

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