Dimethyl Sulfoxide → HCID 79367550, compound

HRID 1880586Notes

Reaction equation

HRID 1880586 reaction equation
CS(C)=O.[H-].[Na+].[I-].C[S+](C)C.[CH3:12][O:13][C:14]1[CH:22]=[C:21]2[C:17]([CH2:18][CH2:19][C:20]2=O)=[CH:16][CH:15]=1.C1C[O:27][CH2:26]C1>O.C(OCC)C>[CH3:12][O:13][C:14]1[CH:22]=[C:21]2[C:17]([CH2:18][CH2:19][CH:20]2[CH:26]=[O:27])=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 3340366-Methoxy-1-Indanone

Product 1

HCID 79367550HCID 79367550, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

A dimethylsulfoxide (8 mL) solution containing sodium hydride (60%, 0.14 g, 3.5 mmol) was heated at 75° C. for ca. 45 minutes. The solution was cooled to room temperature and diluted with THF (8 mL). The solution was cooled to 0° C. and trimethylsulfonium iodide (0.7 g, 3.4 mmol) was added in portions. After 15 minutes a THF solution of 6-methoxyindan-1-one (0.5 g, 3.1 mmol) was added. The solution was then stirred at room temperature for 4 days. The solution was diluted with water and ethyl ether. The organic phase was washed with water (3×) and brine. The solution was then dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 9.68 (d, J=2.9 Hz, 1H); 7.29 (s, 1H); 7.21 (d, J=8.0 Hz, 1H); 6.86-6.82 (m, 1H); 3.95-3.93 (m, 1H); 3.82 (s, 3H); 3.03-2.93 (m, 2H); 2.48-2.44 (m, 1H); 2.41-2.37 (m, 1H). LCMS1 2.90 min. (M+H)=177

Workup

  1. temperatureThe solution was cooled to room temperature
  2. temperatureThe solution was cooled to 0° C.
  3. washThe organic phase was washed with water (3×) and brine
  4. dry with materialThe solution was then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f82a66e2686d44d3a742c6ad471569bb
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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