Water → HCID 14330160, compound

HRID 477402Notes

Reaction equation

HRID 477402 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:25])[CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:12][CH:11]=1.O>CS(C)=O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([CH2:17][O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[CH2:4][O:25]2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 11747188HCID 11747188, compound

Product 1

HCID 14330160HCID 14330160, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

6.3 g (0.21 mol) of sodium hydride (80% strength) are added to a mixture of 42 g (0.19 mol) of trimethylsulphoxonium iodide and 200 ml of dimethylsulphoxide at 15° C. The reaction mixture is stirred at room temperature for 1 hour and a solution of 39 g (0.153 mol) of 1-(4-chlorophenyl)-2-[(tetrahydro-2H-pyran-2-yl)-oxy]-ethan-1-one in 50 ml of dimethylsulphoxide is then added dropwise. The reaction mixture is stirred at 50° C. for 12 hours and then poured into water. The mixture formed is extracted three times with ethyl acetate. The combined organic phases are dried over magnesium sulphate and concentrated by stripping off the solvent under reduced pressure. 37 g (90% of theory) of 2-(4-chlorophenyl)-2-(tetrahydro-2H-pyran-2-yloxy-methyl)-oxirane are obtained in this manner in the form of a pale yellow oil which is used for the subsequent synthesis without additional purification.

Workup

  1. stirringThe reaction mixture is stirred at 50° C. for 12 hours
  2. customThe mixture formed
  3. extractionis extracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3e14c6f906274d2bb945dcb12ba1b698
Source dataset
uspto-grants-1989_12
Patent number
US04888048

Reaction notes

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