Hydrochloric Acid → N-[2-(7,8-dihydro-6H-indeno[4,5-d]-1,3-dioxol-8-yl)ethyl]propionamide

HRID 1636615Notes

Reaction equation

HRID 1636615 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:12]([OH:13])=[C:11]2[C:7]([CH2:8][CH2:9][CH:10]2[CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])=[CH:6][CH:5]=1.I[CH2:22]I.Cl>CN(C)P(N(C)C)(N(C)C)=O.O>[O:13]1[C:12]2[C:11]3[CH:10]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH2:9][CH2:8][C:7]=3[CH:6]=[CH:5][C:4]=2[O:3][CH2:22]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6346DiiodomethaneHCID 24758Sodium hydrideHCID 11043133N-[2-(6,7-dihydroxyindan-1-yl)ethyl]propionamide

Product 1

HCID 10934249N-[2-(7,8-dihydro-6H-indeno[4,5-d]-1,3-dioxol-8-yl)ethyl]propionamideYield 31.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent2×

Procedure

Hexamethyl phosphoramide (5 mL) was cooled with ice, to which was gradually added sodium hydride (0.28 g, 7.5 mmol.), content 65%). To this mixture was added dropwise a solution of N-[2-(6,7-dihydroxyindan-1-yl)ethyl]propionamide (0.85 g, 3.41 mmol.) in hexamethyl phosphoramide (5 mL) at room temperature over 6 minutes. At the time when the bubbling of hydrogen gas ceased, diiodomethane (1.1 g, 4.1 mmol.) was added dropwise to the reaction mixture, followed by stirring for two hours at room temperature. The reaction mixture was poured into water, which was neutralized with dilute hydrochloric acid, followed by extracting the organic matter with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (ethyl acetate) to afford the title compound (yield 280 mg, 31%).

Workup

  1. customAt the time when the bubbling of hydrogen gas
  2. extractionby extracting the organic matter with ethyl acetate
  3. washThe extract solution was washed with a saturated aqueous saline solution and water, which
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe residue was purified by means of silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ef75f0d4ac294a128f4005e5469588eb
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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