Tetrahydrofuran → HCID 22004861, compound

HRID 324612Notes

Reaction equation

HRID 324612 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].O1CCCC1.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[CH:17]([CH2:23][CH2:24][NH2:25])[CH2:16][CH2:15]2.C(N(CC)CC)C>O>[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[CH:17]([CH2:23][CH2:24][NH:25][C:1](=[O:4])[CH2:2][CH3:3])[CH2:16][CH2:15]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 22004826HCID 22004826, compound

Product 1

HCID 22004861HCID 22004861, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Propionyl chloride (2.5 g, 27.0 mmols) was gradually and dropwise added to a tetrahydrofuran (20 ml) solution containing 2-(5-fluoro-6-methoxyindan-1-yl)ethylamine (4.35 g, 20.8 mmols) and triethylamine (4.21 g, 41.6 mmols) while cooling with ice. After having been stirred at room temperature for 2 hours, the reaction mixture was poured into water, and the organic substance was extracted out with ethyl acetate. The extract was washed with a saturated saline solution and water and then dried with anhydrous magnesium sulfate, and the solvent was removed through distillation under reduced pressure. The resulting residue was purified through silica-gel column chromatography (ethyl acetate/hexane=90/10) to obtain 4.87 g (yield: 88%) of the target compound.

Workup

  1. temperaturewhile cooling with ice
  2. extractionthe organic substance was extracted out with ethyl acetate
  3. washThe extract was washed with a saturated saline solution and water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was removed through distillation under reduced pressure
  6. customThe resulting residue was purified through silica-gel column chromatography (ethyl acetate/hexane=90/10)

Sources & evidence

ORD record
ord-4ac28e5bcfea40c89357e52d5d94bc80
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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