Sulfoxonium, trimethyl-, iodide (1:1) → HCID 86704997, compound

HRID 1502620Notes

Reaction equation

HRID 1502620 reaction equation
C[C:2](C)([O-:4])C.[K+].[C:7](=[C:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)([CH3:9])[CH3:8].[I-].C[S+](C)(C)=O>CS(C)=O>[C:7](=[C:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]21[O:4][CH2:2]2)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 126911964-(Propan-2-ylidene)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 86704997HCID 86704997, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium t-butoxide (3.3 g, 29.4 mmol) was added to a mixture of ketone (3, 2.5 g, 18.1 mmol) and trimethylsulfoxonium iodide (6.45 g, 29.4 mmol) in dry dimethyl sulfoxide (40 mL) under nitrogen atmosphere at room temperature. The mixture was stirred for 4.0 h at room temperature. The reaction was quenched by the addition of cold water (40 mL) and extracted with ethyl acetate (2×60 mL). The combined organic layer was washed with water (75 mL) followed by brine (75 mL) and dried over sodium sulfate. The filtered organic layer was concentrated under vacuum to give an oil. Weight: 2.13 g. Weight yield: 77%. 1H-NMR (400 MHz, CDCl3): δ 1.42-1.50 (m, 2H), 1.55-1.61 (m, 2H), 1.65 (s, 6H), 2.31 (t, 4H), 2.61 (s, 2H). MS (APCI method): No molecular ion peak was observed.

Workup

  1. customThe reaction was quenched by the addition of cold water (40 mL)
  2. extractionextracted with ethyl acetate (2×60 mL)
  3. washThe combined organic layer was washed with water (75 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationThe filtered organic layer was concentrated under vacuum
  6. customto give an oil

Sources & evidence

ORD record
ord-ed9b314357764b858370315c32ac74b4
Source dataset
uspto-grants-2015_12
Patent number
US09211269B2

Reaction notes

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