Sodium hydride → HCID 9837050, compound

HRID 2187114Notes

Reaction equation

HRID 2187114 reaction equation
[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[O:15])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[H-].[Na+].C1(S(OC)=O)C=CC=CC=1>O1CCCC1.O>[OH:15][C:10]1[C:9]2[C:8]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:2]([CH3:1])[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 5988759-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-oneHCID 2759784Methyl benzenesulfinate

Product 1

HCID 9837050HCID 9837050, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 9-methyl-4-oxo-1,2,3,4-tetrahydrocarbazole (prepared by the methods described by Osuka, A.; Mori, Y.; Suzuki, H. Chem. Lett. 1982, 2031-2034; and Elz, S.; Heil, W. L. Biorg. Med. Chem. Lett. 1995, 5, 667). (0.20 g, 1.0 mmol) in 3 mL tetrahydrofuran was sonicated and heated to 50° C. Sodium hydride (60% dispersion in mineral oil; 0.07 g, 1.8 mmol) was added in one portion. Sonication and heating was continued for 1 hour and then methyl phenylsulfinate (0.2 g, 1.2 mmol) was added in one portion. The mixture was diluted after 3 hours with retrahydrofuran and water to give a homogenous solution. The solution was concentrated by rotary evaporation and the residue was partitioned between dichloromethane and water. The organic layer was washed with sodium bicarbonate and brine and then dried over magnesium sulfate, filtered and concentrated. The residue was Dissolved in dioxane and heated to reflux for 1 hour. The mixture was concentrated and partitioned between dichloromethane and water. The organic fraction was dried over magnesium sulfate, filtered and concentrated. The mixture was purified by silica gel chromatography (20% EtOAc, hexanes) to 0.075 g of the desired product (38%). TLC Rf=0.49 (20% ethyl acetate, hexanes); 13C NMR (CDCl3) d 151.5, 142.6, 140.1, 126.0, 124.6, 122.4, 121.5, 118.8, 110.7, 107.7, 104.6, 101.0, 28.9; mass spectrum, m/z (FD, M+1) 198.

Workup

  1. customprepared by the methods
  2. customSonication
  3. temperatureheating
  4. customto give a homogenous solution
  5. concentrationThe solution was concentrated by rotary evaporation
  6. customthe residue was partitioned between dichloromethane and water
  7. washThe organic layer was washed with sodium bicarbonate and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. dissolutionThe residue was Dissolved in dioxane
  12. temperatureheated
  13. temperatureto reflux for 1 hour
  14. concentrationThe mixture was concentrated
  15. custompartitioned between dichloromethane and water
  16. dry with materialThe organic fraction was dried over magnesium sulfate
  17. filtrationfiltered
  18. concentrationconcentrated
  19. customThe mixture was purified by silica gel chromatography (20% EtOAc, hexanes) to 0.075 g of the desired product (38%)

Sources & evidence

ORD record
ord-87dd5f946d6c4a7aaf13a59cf47d6e9a
Source dataset
uspto-grants-2002_06
Patent number
US06407261B1

Reaction notes

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