Acetic Anhydride → N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]acetamide

HRID 324636Notes

Reaction equation

HRID 324636 reaction equation
[OH-].[Na+].[C:3](OC(=O)C)(=[O:5])[CH3:4].O1CCCC1.Br.[CH2:16]1[CH2:20][O:19][C:18]2[CH:21]=[CH:22][C:23]3[CH2:24][CH2:25][CH:26]([CH2:28][CH2:29][NH2:30])[C:27]=3[C:17]1=2>O>[CH2:16]1[CH2:20][O:19][C:18]2[CH:21]=[CH:22][C:23]3[CH2:24][CH2:25][CH:26]([CH2:28][CH2:29][NH:30][C:3](=[O:5])[CH3:4])[C:27]=3[C:17]1=2

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 220047782-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine hydrobromide

Product 1

HCID 10890175N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]acetamideYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous 1N sodium hydroxide solution (1.5 ml) and acetic anhydride (0.050 ml, 0.528 mmols) were added to a tetrahydrofuran (1.5 ml) solution of 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine hydrobromide (0.10 g, 0.352 mmols), and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with a saturated saline solution, then dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from isopropyl ether/hexane to obtain 0.057 g (yield: 66%) of the target compound.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe extract was washed with a saturated saline solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from isopropyl ether/hexane

Sources & evidence

ORD record
ord-a6ea8a4a90fc45a8badea176d6fe820c
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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