Methyl Ethyl Ketone → HCID 20250459, compound

HRID 1285255Notes

Reaction equation

HRID 1285255 reaction equation
[CH3:1][C:2]1([C:16]([O:18][CH3:19])=[O:17])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH2:13][CH2:14][CH3:15])[C:6]([OH:12])=[CH:7][CH:8]=2)[O:3]1.[Br:20][CH2:21][CH2:22][CH2:23]Br.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>C(Cl)Cl>[CH3:1][C:2]1([C:16]([O:18][CH3:19])=[O:17])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH2:13][CH2:14][CH3:15])[C:6]([O:12][CH2:23][CH2:22][CH2:21][Br:20])=[CH:7][CH:8]=2)[O:3]1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 20250469HCID 20250469, compound

Product 1

HCID 20250459HCID 20250459, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100 ml single neck round bottom flask was charged with 1.30 g (4.9 mmole) of the compound of Example 24, 11.51 g (57 mmole) of 1,3-dibromopropane, 1.05 g (7.6 mmole) of anhydrous potassium carbonate, and 15 ml of methyl ethyl ketone. The flask was fitted with a magnetic stirring bar and condenser topped with a calcium chloride drying tube and the solution refluxed with stirring for 48 hours. Methylene chloride, 50 ml was added to the flask and insoluble solids were removed by filtration. The volatile solvents were then removed by rotary evaporation and the excess dibromopropane removed at reduced pressure. The crude bromoester was purified by high pressure liquid chromatography (10% ethyl acetate-hexane) to give 1.5 g (79%) of the title compound as a colorless oil. Calc: C, 56.11; H, 6.54, Br, 20.74; Found; C, 56.62, H, 6.52; Br, 20.25.

Workup

  1. customThe flask was fitted with a magnetic stirring bar and condenser
  2. customtopped with a calcium chloride drying tube
  3. temperaturethe solution refluxed
  4. customwere removed by filtration
  5. customThe volatile solvents were then removed by rotary evaporation
  6. customthe excess dibromopropane removed at reduced pressure
  7. customThe crude bromoester was purified by high pressure liquid chromatography (10% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-447a8dc5055a4da9ae9f35a38f5ab7f0
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

Loading…