Dichloromethane → HCID 67484496, compound

HRID 397188Notes

Reaction equation

HRID 397188 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.[O:19]1[CH2:24][CH2:23][CH:22]([OH:25])[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]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)[O:25][CH:22]1[CH2:23][CH2:24][O:19][CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 74956Tetrahydro-4H-pyran-4-olHCID 72952160Methyl 2-diazo-2-(3,4-dichlorophenyl)acetate

Product 1

HCID 67484496HCID 67484496, compoundYield 75%

Reagents, catalysts & solvents 2

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

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, 614 mg, 2.51 mmol), dichloromethane (10 mL) and tetrahydro-4H-pyran-4-ol (0.50 mL, 5.01 mmol). The solution was stirred at 25° C. and then rhodium (II) acetate dimer (22 mg, 0.05 mmol) was added. Gas evolution began immediately 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 (10 mL) 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 in vacuo. The residual material was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 98/2 hexanes/ethyl acetate) to furnish rac-(3,4-dichloro-phenyl)-[(tetrahydro-pyran-4-yl)oxy]-acetic acid methyl ester (598 mg, 75% yield) as a clear colorless oil: EI-HRMS m/e calcd for C14H16Cl2O4 (M+) 318.0426, found 318.0412.

Workup

  1. customIn a dry 25 mL round bottom flask under argon was placed
  2. stirringAfter the solution was stirred at 25° C. for 1 h
  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 and in vacuo
  6. customThe residual material was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 98/2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-55d99a6a50b14eda840176d52f43a331
Source dataset
uspto-grants-2003_08
Patent number
US06608218B2

Reaction notes

Loading…