Indole → HCID 22907241, compound

HRID 2258585Notes

Reaction equation

HRID 2258585 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 8028TetrahydrofuranSolvent2×

Procedure

An ice cooled solution of indole (9 g, 78 mmol) in dry THF (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-6e7466a4ed5940d195dbc719d7125fc2
Source dataset
uspto-grants-1997_08
Patent number
US05661173

Reaction notes

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