Dimethyl Sulfide → HCID 23291935, compound

HRID 365534Notes

Reaction equation

HRID 365534 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:17])([CH3:16])[CH2:7][C:8](=O)[N:9]2[CH:12]([CH3:14])[CH3:13])=[CH:4][C:3]=1[CH3:18].S(C)C.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:16])([CH3:17])[CH2:7][CH2:8][N:9]2[CH:12]([CH3:13])[CH3:14])=[CH:4][C:3]=1[CH3:18]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 10340Sodium CarbonateHCID 21966430HCID 21966430, compound2×

Product 1

HCID 23291935HCID 23291935, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7-Bromo-1-isopropyl-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one (Compound 43, 50 g, 161.2 mmol) was dissolved in toluene (300 mL) and the solution was cooled to 0° C. and treated with 2.0 M of BH3.SMe2 (20 mL, 193.44 mmol) in THF. The solution was stirred at 0° C. for 1 hour and at room temperature over night, and at 60° C. for 1 day. Thereafter the reaction mixture was treated with 10% aqueous Na2CO3. The solution was stirred at room temperature for 1 hour, the layers were separated and the aqueous layer extracted twice with ethyl acetate. The combined organic layers were washed with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (2% ethyl acetate in hexane, Rf=0.35) to give the title compound (37.8 g, 79% over 4 steps) as an oil:

Workup

  1. additiontreated with 2.0 M of BH3
  2. waitat 60° C. for 1 day
  3. stirringThe solution was stirred at room temperature for 1 hour
  4. customthe layers were separated
  5. extractionthe aqueous layer extracted twice with ethyl acetate
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (2% ethyl acetate in hexane, Rf=0.35)

Sources & evidence

ORD record
ord-e9b58ecd3ab6484d89cb0186b74f4a51
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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