Water → HCID 67484331, compound

HRID 397183Notes

Reaction equation

HRID 397183 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.[CH:16]1([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.O>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH3:1][O:2][C:3](=[O:15])[CH:4]([O:22][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7966CyclohexanolHCID 72952160Methyl 2-diazo-2-(3,4-dichlorophenyl)acetate

Product 1

HCID 67484331HCID 67484331, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

In a dry 25 mL round bottom flask under argon was placed diazo-(3,4-dichloro-phenyl)-acetic acid methyl ester (from Example 1, 550 mg 2.24 mmol) and cyclohexanol (0.47 mL, 4.49 mmol) in dichloromethane (10 mL). The solution was stirred at 25° C. and as rhodium (II) acetate dimer (20 mg, 0.045 mmol) was added, the immediate evolution of gas was observed and the color changed from bright yellow to an aquagreen color. After the solution was stirred at 25° C. for 1 h, it was poured into water and the layers were separated. The aqueous layer was washed with dichloromethane (3×15 mL) and the combined organic layers were dried over sodium sulfate and evaporated under reduced pressure. The residual oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 98/2 hexanes/ethyl acetate) to furnish rac-cyclohexyloxy-(3,4-dichloro-phenyl)-acetic acid methyl ester (527 mg, 74% yield) as a clear colorless oil: EI-HRMS m/e calcd for C15H18Cl2O3 (M+) 316.0633, found 316.0646.

Workup

  1. customIn a dry 25 mL round bottom 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 materialthe combined organic layers were dried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residual oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 98/2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-f6068ccbb4f0427e86197f5afab9665a
Source dataset
uspto-grants-2003_08
Patent number
US06608218B2

Reaction notes

Loading…