Ethylene Glycol → HCID 59545165, compound

HRID 1892875Notes

Reaction equation

HRID 1892875 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:7]2.[C:19]1(B(O)O)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)CO>O>[C:19]1([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:10]=2[C:9](=[O:11])[CH:8]([CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:7]3)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 58444101HCID 58444101, compound

Product 1

HCID 59545165HCID 59545165, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

18.5 g (70.4 mmole) 7-Chloro-2-cyclohexylmethyl-indan-1-one, 14.5 g (1.2 eq.) naphthyl boronic acid, 16.4 g sodium carbonate, 230 ml ethylene glycol and 45 ml water were placed in a 1 l—roundbottom flask equipped with a mechanical stirrer and a reflux condenser. The mixture was degassed three times by slight evacuation and recharging with argon. A premixed catalyst solution consisting of 32 mg (0.2 mole %) palladium acetate, 0.94 ml NaTPPTS (2.6 M in water, 0.8 mole %) and 3 ml of water was added and the mixture was refluxed at 125° C. until complete conversion (approx. 5 h). 100 ml of water were added and the mixture was extracted three times with 100 ml of toluene each. The combined organic layers were washed twice with 100 ml water and once with 100 ml of a saturated sodium chloride solution. Drying over magnesium sulphate and evaporation of the solvent in vacuo yielded 24 g (96%) of the desired product as a yellow sticky oil. 1H-NMR (400 MHz, CDCl3): δ=7.86 (d, 2 h, aromatic), 7.63 (m, 1H, aromatic), 7.52 (m, 2H, aromatic), 7.43 (m, 2H, aromatic), 7.33 (m, 3H, aromatic), 2.39 (m, 1H, (C═O)CH), 2.85, 2.67 (2×m, 2H, benzylic), 1.90-0.80 (m, 13H, aliphatic) ppm.

Workup

  1. customequipped with a mechanical stirrer and a reflux condenser
  2. customThe mixture was degassed three times by slight evacuation
  3. additionwas added
  4. addition100 ml of water were added
  5. extractionthe mixture was extracted three times with 100 ml of toluene each
  6. washThe combined organic layers were washed twice with 100 ml water and once with 100 ml of a saturated sodium chloride solution
  7. dry with materialDrying over magnesium sulphate and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-26a4a0f25a9744fba23cf81c7ddd2f18
Source dataset
uspto-grants-2013_08
Patent number
US08507706B2

Reaction notes

Loading…