Dichloromethane → HCID 69082969, compound

HRID 594376Notes

Reaction equation

HRID 594376 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([O:15][CH3:16])[CH:8]=1.Cl[C:18](=[O:26])[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].C(Cl)Cl>ClCCCl>[O:26]=[C:18]([C:8]1[C:9]([O:15][CH3:16])=[CH:10][C:11]([O:13][CH3:14])=[CH:12][C:7]=1[O:6][CH3:5])[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 693011,3,5-TrimethoxybenzeneHCID 73916Methyl 4-chloroformylbutyrateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 69082969HCID 69082969, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) suspension of aluminum chloride (9.316 g; 69.87 mmol) in anh. DCE (50 ml) was treated with commercially available 1,3,5-trimethoxybenzene (7.664 g; 45.56 mmol), and stirring at 0° C., under nitrogen, was continued for 10 min. Commercially available methyl 5-chloro-5-oxopentanoate (5.000 g; 30.37 mmol) was then added, and the mixture was stirred at rt for 26 h. The resulting reaction mixture was poured onto crushed ice (150 g), and DCM (100 ml) was added. The separated aq. layer was further extracted with DCM (3×50 ml). The mixed organic layers were washed successively with water (75 ml) and brine (2×75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=10/1 to AcOEt) afforded methyl 5-oxo-5-(2,4,6-trimethoxyphenyl)pentanoate as a yellow oil. LC-MS (conditions D): tR=0.94 min.; [M+H]+: 297.13 g/mol.

Workup

  1. temperatureA cooled
  2. stirringthe mixture was stirred at rt for 26 h
  3. customThe resulting reaction mixture
  4. additionwas poured
  5. additionwas added
  6. extractionThe separated aq. layer was further extracted with DCM (3×50 ml)
  7. washThe mixed organic layers were washed successively with water (75 ml) and brine (2×75 ml)
  8. dry with materialdried over anh. MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure
  11. customPurification by FC (heptane/AcOEt=10/1 to AcOEt)

Sources & evidence

ORD record
ord-207064578f9444e8b851676b3c64c8c1
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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