Iodoethane → 5-Ethoxy-2,3-dihydro-1H-inden-1-one

HRID 402507Notes

Reaction equation

HRID 402507 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH3:19]>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2)[CH3:19]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 2331475-Hydroxy-1-indanone

Product 1

HCID 227325585-Ethoxy-2,3-dihydro-1H-inden-1-oneYield 99.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Hydroxy-1-indanone (2.5 g, 16.0 mmol) was dissolved in acetone (60 ml) and potassium carbonate (waterfree, 5.15 g, 36.9 mmol) and ethyl iodide (2.88 ml, 35.3 mmol) were added. The reaction was stirred at it under an atmosphere of nitrogene for 6 days. The mixture was filtered, the filtrate collected and the solvent evaporated at reduced pressure. Chromatography on silica (flashmaster, hex to hex/EtOAc 2/3 in 20 min, 15 min hex/EtOAc 2/3) gave the product as off-white solid (2.8 g, 99%). [1H-NMR (DMSO-d6, 600 MHz) δ 7.54 (d, 1H), 7.07 (s, 1H), 6.94 (d, 1H), 4.13 (q, 2H), 3.05-3.03 (m, 2H), 2.58-2.56 (m, 2H), 1.35 (t, 3H); LCMS RtJ=0.88 min; [M+H]+=177.2]

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate collected
  3. customthe solvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-ad4886f41bd34e478bb4747d9d2b0d86
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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