Tetrahydrofuran → HCID 22004861, compound

HRID 1636585Notes

Reaction equation

HRID 1636585 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-8c51b5765cd94a8b94b3859ce81ef3a6
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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