Dimethylformamide → HCID 67486253, compound

HRID 534082Notes

Reaction equation

HRID 534082 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+].[CH3:17]N(C=O)C>>[CH3:17][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

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 13128614[(2S,3S)-1,4-Dioxaspiro[4.5]decane-2,3-diyl]dimethanol

Product 1

HCID 67486253HCID 67486253, compoundYield 45.03%

Procedure

(2S,3S)-1,4-dioxaspiro[4.5]decane-2,3diyldimethanol (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. Idomethane (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]decane-2-yl)methanol (3.13 g, 144.7 mmol, 45.03% yield) as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. additionIdomethane (20.05 ml, 321.4 mmol) was added
  3. stirringthe reaction was stirred at ambient temperature overnight
  4. customThe majority of the DMF was removed on a rotary evaporator
  5. customthe residue was partitioned between aqueous NH4Cl and EtOAc
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified over 1 Kg of SiO2 (20 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-153c3bb007554a86a358f1681dab9028
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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