Potassium Carbonate → HCID 21100037, compound

HRID 1352195Notes

Reaction equation

HRID 1352195 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.I[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:13]([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)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123801-IodooctaneHCID 2331475-Hydroxy-1-indanone

Product 1

HCID 21100037HCID 21100037, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-hydroxy-1-indanone (1.00 g, 6.74 mmol), 1-iodooctane (1.34 mL, 7.42 mmol) and potassium carbonate (1.40 g, 10.12 mmol) were stirred together in acetonitrile at 80° C. After 3 h, the reaction was cooled, placed onto silica gel and eluted with 15% ethyl acetate/hexane to give 1.14 g of a white solid: 1H NMR (500 MHz, CDCl3): δ 7.67 (d, J=9.2 Hz, 1H), 6.88–6.90 (m, 2H), 4.03 (t, J=6.55 Hz, 2H), 3.08 (t, J=5.9 Hz, 2H), 2.67 (t, J=6.0 Hz, 2H), 1.80 (m, 2H), 1.42–1.50 (m, 2H), 1.24–1.38 (m, 8H), 0.89 (t, J=7.0 Hz, 3H); ESI-MS 261.1 (M+H).

Workup

  1. temperaturethe reaction was cooled
  2. washeluted with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a5bfb2d16b37489d8431dea3c42287a6
Source dataset
uspto-grants-2007_05
Patent number
US07220734B2

Reaction notes

Loading…