Diethyl Ether → Methyl indane-2-carboxylate

HRID 984099Notes

Reaction equation

HRID 984099 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10](S)[CH:11]=2)[CH2:6]1)=[O:4].ClCC1SC(C2C=CC(C(F)(F)F)=CC=2)=NC=1C.[Cl-].C([O-])([O-])=O.[Cs+].[Cs+].CCOCC>C(#N)C.O>[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 207660125-Mercapto-Indan-2-Carboxylic Acid Methyl EsterHCID 21949469Chloride 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

Product 1

HCID 9964238Methyl indane-2-carboxylateYield 68.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 1C (crude mixture from above, 830 mg) was dissolved in acetonitrile (80 mL) with the chloride 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (0.50 g, 1.71 mmol) and Cs2CO3 (2.37 g, 7.27 mmol) The reaction mixture was stirred at RT overnight. Ether (50 mL) and H2O were added and stirring was continued for another 5 min. The layers were separated and the aqueous layer was extracted with ether (2×100 mL). The combined organics was dried over MgSO4 and concentrated to an oil. The crude product was purified by column chromatography eluted with EtOAc and hexanes to give the desired product as a thick yellow oil (0.48 g, 28% for 2 steps).

Workup

  1. stirringstirring
  2. waitwas continued for another 5 min
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether (2×100 mL)
  5. dry with materialThe combined organics was dried over MgSO4
  6. concentrationconcentrated to an oil
  7. customThe crude product was purified by column chromatography
  8. washeluted with EtOAc and hexanes

Sources & evidence

ORD record
ord-b11fc74cb8e4429d986ab6c78c31ff56
Source dataset
uspto-grants-2005_03
Patent number
US06867224B2

Reaction notes

Loading…