Sodium hydride → HCID 19068948, compound

HRID 1957224Notes

Reaction equation

HRID 1957224 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>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

5

Reactant 3

HCID 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 reaciton continued another 4 hours. The reaction mixture was added to a 2N K2 CO3 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 reaciton continued another 4 hours
  3. additionThe reaction mixture was added to a 2N K2 CO3 solution
  4. extractionextracted with toluene
  5. washThe organic phase was washed with water and brine
  6. customdried
  7. customevaporated
  8. extractionThe resulting oil was extracted twice with boiling heptane
  9. temperaturecooled
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-09eb83c0dd144f78b672abe548188456
Source dataset
uspto-grants-1998_07
Patent number
US05783575

Reaction notes

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