Sulfoxonium, trimethyl-, iodide (1:1) → (5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)oxirane

HRID 1591125Notes

Reaction equation

HRID 1591125 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7][C:8]([O-:11])(C)[CH3:9].[K+].[CH3:13][C:14]1([CH3:28])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]2[CH:19]=C(C=O)[CH:17]=[CH:16][C:15]1=2>CS(C)=O.O1CCCC1>[CH3:13][C:14]1([CH3:28])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]2[CH:19]=[C:7]([CH:8]3[CH2:9][O:11]3)[CH:17]=[CH:16][C:15]1=2

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 104208875,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 14726539(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)oxirane

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

33 g (0.15 mole) of trimethylsulfoxonium iodide were added at room temperature to a solution of 17 g (0.15 mole) of potassium tert-butylate in 150 ml of dried dimethyl sulfoxide. The mixture was stirred for 0.5 hour, after which a solution of 32.5 g (0.15 mole) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthaldehyde in 100 ml of tetrahydrofuran was added dropwise. Stirring was continued for 1 hour, after which the mixture was poured onto water and extracted with ether. The organic phase was washed with water, dried over magnesium sulfate and evaporated down. 31.3 g of (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-oxirane remained. The structure was determined by H-NMR spectroscopy.

Workup

  1. stirringStirring
  2. waitwas continued for 1 hour
  3. additionafter which the mixture was poured onto water
  4. extractionextracted with ether
  5. washThe organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated down

Sources & evidence

ORD record
ord-2115fb576b29471194efe97f3f249733
Source dataset
uspto-grants-1993_04
Patent number
US05206242

Reaction notes

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