Water → 8-(Oxiran-2-yl)-1,4-dioxaspiro[4.5]decane

HRID 2063737Notes

Reaction equation

HRID 2063737 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[O:9]1[C:13]2([CH2:18][CH2:17][CH:16]([CH:19]=[O:20])[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1.O>CS(C)=O>[O:20]1[CH2:4][CH:19]1[CH:16]1[CH2:17][CH2:18][C:13]2([O:12][CH2:11][CH2:10][O:9]2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 98989471,4-Dioxaspiro(4.5)decane-8-carbaldehyde

Product 1

HCID 585624888-(Oxiran-2-yl)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A 60% strength dispersion of sodium hydride in mineral oil (1.78 g, 44.59 mmol) was taken up in dimethylsulfoxide (25 ml), and trimethylsulfoxonium iodide (9.80 g, 44.6 mmol) was added. The mixture was stirred at room temperature for 45 min. A solution of 1,4-dioxaspiro[4,5]decane-8-carbaldehyde (7.59 g, 44.6 mmol) in dimethylsulfoxide (20 ml) was then added to the mixture. The reaction mixture was stirred at 60° C. for 18 h. After cooling, the mixture was poured into water (100 ml) and extracted with diethyl ether (4×20 ml). The combined organic phases were dried with sodium sulfate and concentrated in vacuo. The crude product (4.64 g) was purified by flash chromatography with cyclohexane/ethyl acetate (4:1).

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 18 h
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether (4×20 ml)
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product (4.64 g) was purified by flash chromatography with cyclohexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-0817fcf59ebb45e4b8b7343cac036109
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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