HCID 89601123, compound → HCID 89607242, compound

HRID 514213Notes

Reaction equation

HRID 514213 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH3:10])[CH:5]=[C:4]([O:11][CH3:12])[C:3]=1[C:13]1[C:14](=[O:23])[CH:15]([CH2:20][C:21]#[CH:22])[CH2:16][C:17]=1[O:18]C>CC(C)=O.Cl.ClCCl.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH3:10])[CH:5]=[C:4]([O:11][CH3:12])[C:3]=1[CH:13]1[C:14](=[O:23])[CH:15]([CH2:20][C:21]#[CH:22])[CH2:16][C:17]1=[O:18]

Participants

6

Reactant 1

HCID 89601123HCID 89601123, compound

Product 1

HCID 89607242HCID 89607242, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2-chloro-6-methoxy-4-prop-1-ynyl-phenyl)-3-methoxy-5-prop-2-ynyl-cyclopent-2-en-1-one (0.042 g, 0.1277 mmol) in acetone (1.5 mL) and 2M aqueous HCl (0.5 mL) was heated under microwave irradiation at 100°C. for 30 minutes. The reaction mixture was allowed to cool to room temperature, and then was diluted with dichloromethane (5 ml) and water (5 ml), and then was separated by elution through a phase separation cartridge, washing with more dichloromethane. The organic filtrate was evaporated to dryness under reduced pressure to give a yellow solid. The crude product was dissolved in dichloromethane and adsorbed onto silica and then purified by flash chromatography over silica using an EtOAc/isohexane gradient to give the desired product as a mixture of atropisomers. 1H NMR (400 MHz, CDCl3) δ ppm 7.13 (s, 1H), 6.85 (s, 1H), 3.79 (s, 3H), 2.99-2.56 (m, 5H), 2.06 (s, 3H), 2.00 (s, 1H).

Workup

  1. customwas separated by elution through a phase separation cartridge
  2. washwashing with more dichloromethane
  3. customThe organic filtrate was evaporated to dryness under reduced pressure
  4. customto give a yellow solid
  5. custompurified by flash chromatography over silica using an EtOAc/isohexane gradient

Sources & evidence

ORD record
ord-ed7f85bf06264ecaa1f3db852e1c5181
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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