Dichloromethane → Rac-cyclopentyloxy-(3,4-dichloro-phenyl)-acetic acid methyl ester

HRID 1019195Notes

Reaction equation

HRID 1019195 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4](=[N+]=[N-])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1.ClCCl.[CH:19]1([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20]1>CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh].O>[CH3:1][O:2][C:3](=[O:15])[CH:4]([O:24][CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 7298CyclopentanolHCID 72952160Methyl 2-diazo-2-(3,4-dichlorophenyl)acetate

Product 1

HCID 12044173Rac-cyclopentyloxy-(3,4-dichloro-phenyl)-acetic acid methyl esterYield 64.3%

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

In a dry flask under argon was placed diazo-(3,4-dichloro-phenyl)-acetic acid methyl ester (350 mg 1.4 mmol) to which was added dichloromethane (10 mL) and cyclopentanol (0.25 mL, 2.8 mmol). The solution was stirred at 25° C. and as rhodium (II) acetate dimer (13 mg, 0.028 mmol) was added, the immediate evolution of gas was noted and the color changed from bright yellow to an aquagreen color. After the solution was stirred at 25° C. for 1 h, it was then poured into water and the layers were separated. The aqueous layer was washed with dichloromethane (3×15 mL) and the organic layers were then combined, dried over sodium sulfate and concentrated in vacuo. The residual material was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 hexanes/ethyl acetate) to give rac-cyclopentyloxy-(3,4-dichloro-phenyl)-acetic acid methyl ester (273 mg, 64% yield) as a clear colorless oil: EI-HRMS m/e calcd for C14H16Cl2O3 (M+) 302.0477, found 302.0484.

Workup

  1. customIn a dry flask under argon was placed
  2. additionwas added
  3. customthe layers were separated
  4. washThe aqueous layer was washed with dichloromethane (3×15 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residual material was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-cfad19bfab5d4a5ca0d8f54a5c1ce29e
Source dataset
uspto-grants-2002_11
Patent number
US06486184B2

Reaction notes

Loading…