Methyl iodide → HCID 67486253, compound

HRID 1511102Notes

Reaction equation

HRID 1511102 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:4][C@@H:3]([CH2:11][OH:12])[C@@H:2]1[CH2:13][OH:14].[H-].[Na+].I[CH3:18]>CN(C=O)C>[CH3:18][O:12][CH2:11][C@@H:3]1[O:4][C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:1][C@H:2]1[CH2:13][OH:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13128614[(2S,3S)-1,4-Dioxaspiro[4.5]decane-2,3-diyl]dimethanol

Product 1

HCID 67486253HCID 67486253, compoundYield 45.03%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S,3S)-1,4-dioxaspiro[4.5]decane-2,3-diyldimethanol (65 g, 321.4 mmol) was dissolved in DMF (500 mL) and cooled in an ice bath. 60% Sodium hydride (15.43 g, 385.7 mmol) was added slowly and the reaction was stirred for 30 minutes in an ice bath then warmed to ambient temperature for 2 hours. Iodomethane (20.05 ml, 321.4 mmol) was added and the reaction was stirred at ambient temperature overnight. The majority of the DMF was removed on a rotary evaporator, and the residue was partitioned between aqueous NH4Cl and EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified over 1 Kg of SiO2 (20 to 40% EtOAc in hexanes) to afford ((2S,3S)-3-(methoxymethyl)-1,4-dioxaspiro[4.5]decan-2-yl)methanol (31.3 g, 144.7 mmol, 45.03% yield) as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe reaction was stirred at ambient temperature overnight
  3. customThe majority of the DMF was removed on a rotary evaporator
  4. customthe residue was partitioned between aqueous NH4Cl and EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified over 1 Kg of SiO2 (20 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fba6c2100d594275bc90c5d97684388a
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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