Water → 2-{2-[4-(1,3-Dioxolan-2-yl)-phenyl]-ethenyl}-2-tert.-butyl-oxirane

HRID 652580Notes

Reaction equation

HRID 652580 reaction equation
I[CH3:2].CSC.[CH3:6][C:7]([CH3:24])([CH3:23])[C:8](=[O:22])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[O:21][CH2:20][CH2:19][O:18]2)=[CH:13][CH:12]=1.O>CS(C)=O.O1CCCC1>[O:21]1[CH2:20][CH2:19][O:18][CH:17]1[C:14]1[CH:15]=[CH:16][C:11]([CH:10]=[CH:9][C:8]2([C:7]([CH3:24])([CH3:23])[CH3:6])[CH2:2][O:22]2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 6328Methyl iodideHCID 543458391-[4-(1,3-Dioxolan-2-yl)phenyl]-4,4-dimethylpent-1-en-3-one

Product 1

HCID 201978292-{2-[4-(1,3-Dioxolan-2-yl)-phenyl]-ethenyl}-2-tert.-butyl-oxiraneYield 93.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

8.1 g (0.13 mol) of iodomethane are slowly added dropwise to a solution of 9.9 ml (0.135 mol) of dimethyl sulphide in 75 ml of absolute dimethylsulphoxide and 35 ml of absolute tetrahydrofuran, during which the internal temperature must not rise above 35° C. This suspension is subsequently stirred at room temperature overnight, and 15.7 g (0.14 mol) of potassium tert.-butylate are then added in portions. The mixture is subsequently stirred at room temperature for 30 minutes and cooled to 0° C., and 26 g (0.1 mol) of 4,4-dimethyl-1-[4-(1,3-dioxolan-2-yl)phenyl]-1-penten-3-one are added in portions. The reaction mixture is subsequently stirred at room temperature overnight, water is then added and the mixture is extracted three times with toluene. The combined toluene phases are washed with water and saturated sodium chloride solution, dried over sodium sulphate and concentrated. 25.6 g of crude 2-{2-[4-(1,3-dioxolan-2-yl)-phenyl]-ethenyl} -2-tert.-butyl-oxirane are obtained as an oil, which is further reacted directly. ##STR26##

Workup

  1. customrise above 35° C
  2. stirringThe mixture is subsequently stirred at room temperature for 30 minutes
  3. temperaturecooled to 0° C.
  4. stirringThe reaction mixture is subsequently stirred at room temperature overnight
  5. extractionthe mixture is extracted three times with toluene
  6. washThe combined toluene phases are washed with water and saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-037bc437145944319a14c15d75cb8025
Source dataset
uspto-grants-1987_06
Patent number
US04672134

Reaction notes

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