Potassium Carbonate → HCID 19068948, compound

HRID 1735120Notes

Reaction equation

HRID 1735120 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[Cl:13])(=[O:3])[CH3:2].[H-].[Na+].[CH3:16][O:17][CH2:18][CH2:19][O:20][CH2:21]Cl.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:5]=1[Cl:13])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydride2×HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 109323071-(2-Chloro-1H-indol-3-yl)ethan-1-one

Product 1

HCID 19068948HCID 19068948, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g of (75) was dissolved in 25 ml THF. 250 mg NaH was added, and then 1.87 g of (2-methyloxyethyl)oxymethylchlorid. The reaction was left with stirring overnight, another 100 mg NaH was added, and the reaction continued another 4 hours. The reaction mixture was added to a 2N K2CO3 solution and extracted with toluene. The organic phase was washed with water and brine, dried and evaporated. The resulting oil was extracted twice with boiling heptane, cooled, filtered, and evaporated giving 1.23 g of (80) as a yellow oil, 1H-NMR (ppm): 8.35(m, 1H); 7.44(m, 1H); 7.27(m, 2H); 5.62(s, 2H); 3.58(m, 2H); 3.47(m, 2H); 3.32(s, 3H); 2.65(s, 3H).

Workup

  1. waitThe reaction was left
  2. waitthe reaction continued another 4 hours
  3. extractionextracted with toluene
  4. washThe organic phase was washed with water and brine
  5. customdried
  6. customevaporated
  7. extractionThe resulting oil was extracted twice with boiling heptane
  8. temperaturecooled
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-b90a7a4e16514c5c8a86237624ca39e8
Source dataset
uspto-grants-1996_07
Patent number
US05536721

Reaction notes

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