HCID 10883054, compound → HCID 11068552, compound

HRID 324647Notes

Reaction equation

HRID 324647 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:12][C:13]([CH3:15])=[CH2:14])[C:10]=1[OH:11])[CH:7]([CH2:16][CH2:17][NH:18][C:19](=[O:22])[CH2:20][CH3:21])[CH2:6][CH2:5]2>C(Cl)Cl>[Br:1][C:2]1[C:10]2[O:11][C:13]([CH3:15])([CH3:14])[CH2:12][C:9]=2[C:8]2[CH:7]([CH2:16][CH2:17][NH:18][C:19](=[O:22])[CH2:20][CH3:21])[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 10883054HCID 10883054, compound

Product 1

HCID 11068552HCID 11068552, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[2-(5-bromo-6-hydroxy-7-(2-methyl-2-propenyl)indan-1-yl)ethyl]propionamide (2.4 g, 6.5 mmol.) in methylene chloride (40 mL) was cooled with ice. To the solution was added dropwise gradually a diethyl ether boron trifluoride complex (4.0 mL, 32.5 mmol.). The reaction mixture was stirred for 3 hours under ice-cooling, which was poured into ice-water, followed by extracting the organic matter with ethyl acetate. The extract solution was washed with water and a saturated aqueous solution of sodium hydrogencarbonate, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was recrystallized from ethyl acetate/isopropyl ether to afford the title compound (yield 2.1 g, 89%).

Workup

  1. additionTo the solution was added dropwise gradually a diethyl ether boron trifluoride complex (4.0 mL, 32.5 mmol.)
  2. temperaturecooling
  3. extractionby extracting the organic matter with ethyl acetate
  4. washThe extract solution was washed with water
  5. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, which was dried over anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-5893947330ac47d9b8f3956488de18c4
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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