Dimethylformamide → HCID 18355159, compound

HRID 429661Notes

Reaction equation

HRID 429661 reaction equation
CC1(C)CCCC(C)(C)N1.C([Li])CCC.[CH3:16][O:17][CH2:18][O:19][N:20]1[C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([C:29]([O:31][CH3:32])=[O:30])[C:23]=2[CH:22]=[CH:21]1.CN(C)[CH:35]=[O:36]>O1CCCC1>[CH:35]([C:21]1[N:20]([O:19][CH2:18][O:17][CH3:16])[C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([C:29]([O:31][CH3:32])=[O:30])[C:23]=2[CH:22]=1)=[O:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 130352,2,6,6-TetramethylpiperidineHCID 18355067HCID 18355067, compoundHCID 178418339Butyllithium

Product 1

HCID 18355159HCID 18355159, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 2,2,6,6-tetramethylpiperidine (1.97 g) in tetrahydrofuran (24.0 ml) was added dropwise n-butyllithium (6.8 ml, 1.64M solution in n-hexane) at −40° C. and the mixture was stirred at 0° C. for 30 minutes. A solution of methyl 1-methoxymethoxyindole-4-carboxylate (1.64 g) in tetrahydrofuran (12.0 ml) was added t the above solution at −60° C. and the solution was stirred at the same temperature for 30 minutes. A solution of N,N-dimethylformamide (662 mg) in tetrahydrofuran (9.0 ml) was added to the reaction mixture at −60° C. and the solution was stirred at the same temperature for 2 hours. The temperature was raised to −320° C. and the reaction was quenched with saturated ammonium chloride aqueous solution. The aqueous solution was extracted with ethyl acetate (80 ml) and the organic layer was washed with brine. Drying, filtering and removal of solvents afforded a crude product. The crude product was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to give methyl 2-formyl-1-methoxymethoxyindole-4-carboxylate (1.15 g).

Workup

  1. stirringthe solution was stirred at the same temperature for 30 minutes
  2. stirringthe solution was stirred at the same temperature for 2 hours
  3. temperatureThe temperature was raised to −320° C.
  4. customthe reaction was quenched with saturated ammonium chloride aqueous solution
  5. extractionThe aqueous solution was extracted with ethyl acetate (80 ml)
  6. washthe organic layer was washed with brine
  7. customDrying
  8. filtrationfiltering
  9. customremoval of solvents
  10. customafforded a crude product
  11. customThe crude product was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-1635d0c0d9074484a3c0b9fdb81be222
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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