Indole → HCID 22907241, compound

HRID 1077940Notes

Reaction equation

HRID 1077940 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Br[CH:13]1[CH2:18][CH2:17][O:16][C:14]1=[O:15]>C1COCC1>[N:1]1([CH:13]2[CH2:18][CH2:17][O:16][C:14]2=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 22907241HCID 22907241, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An ice cooled solution of indole (9 g, 78 mmol) in dry THP (80 mL) was treated with oil free sodium hydride (2.25 g, 94 mmol). After 1 hour, a solution of 2-bromobutyrolactone (14.6 mL, 78 mmol) in dry THF (20 mL) was added dropwise. After stirring overnight at ambient temperature, the mixture was poured on crushed ice, extracted with ethyl acetate (3×), dried, and evaporated. The residue was purified by flash chromatography on silica gel with a hexane/ethyl acetate gradient (9:1 to 7:3). Evaporation of the eluting solvent gave 8 g of a yellowish oil (52% of theory).

Workup

  1. additionthe mixture was poured
  2. customon crushed ice
  3. extractionextracted with ethyl acetate (3×)
  4. customdried
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel with a hexane/ethyl acetate gradient (9:1 to 7:3)
  7. customEvaporation of the eluting solvent

Sources & evidence

ORD record
ord-3c5a3b4d440741b9a7fa2e28278f1b07
Source dataset
uspto-grants-1996_08
Patent number
US05545636

Reaction notes

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