Sodium hydride → 3022954-52-2

HRID 715511Notes

Reaction equation

HRID 715511 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[O:9]=[C:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]1>CS(C)=O.O>[O:9]1[C:10]2([CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2)[CH2:2]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 566099Methyl 3-oxocyclohexane-1-carboxylate

Product 1

HCID 867165813022954-52-2Yield 100.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of trimethylsulfoxonium iodide (53.3 g, 242 mmol) in dry DMSO (300 mL) under N2, was added sodium hydride (9.69 g, 242 mmol) portionwise over 30 min. This light yellow mixture was stirred at RT for 1 h. The reaction mixture was then cooled in an ice bath and treated with methyl 3-oxocyclohexanecarboxylate (29.0 g, 186 mmol) dropwise while maintaining a temperature at or below 27° C. The resulting reaction mixture was allowed to warm slowly to RT and stir overnight. The reaction was diluted with water and extracted with DCM. The combined organics were washed with water, dried over MgSO4, filtered, and concentrated to provide methyl 1-oxaspiro[2.5]octane-5-carboxylate (31.8 g, 85% yield) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 3.66 (s, 3H), 2.71 (m, 1H), 2.65 (d, J=1.76 Hz, 2H), 2.00 (dd J=11.8, 13.6 Hz, 2H), 1.74-1.85 (m, 2H), 1.60-1.74 (m, 1H), 1.40-1.56 (m, 2H), 1.17-1.32 (m, 1H).

Workup

  1. temperatureThe reaction mixture was then cooled in an ice bath
  2. temperaturewhile maintaining a temperature at or below 27° C
  3. customThe resulting reaction mixture
  4. temperatureto warm slowly to RT
  5. stirringstir overnight
  6. extractionextracted with DCM
  7. washThe combined organics were washed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-48debdb4355c4618b6b490fa2f56e300
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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