Iodoethane → HCID 67538067, compound

HRID 2241013Notes

Reaction equation

HRID 2241013 reaction equation
[F:1][CH:2]([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:24])[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[C:20][CH2:21][CH2:22][OH:23])[CH:14]=2)=[O:12])=[CH:6][CH:5]=1.[OH-].[Na+].[CH2:28](I)C.CCOC(C)=O>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[F:1][CH:2]([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:24])[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[C:20][CH2:21][CH2:22][O:23][CH3:28])[CH:14]=2)=[O:12])=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl Acetate2×HCID 14798Sodium HydroxideHCID 67538230HCID 67538230, compound

Product 1

HCID 67538067HCID 67538067, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-(difluoromethoxy)phenyl)-2-(3-(4-hydroxybut-1-ynyl)phenyl)ethane-1,2-dione (344 mg, 1.0 mmol) from the previous step in DCM (5 mL) was added tetrabutylammonium bromide (64 mg, 0.2 mmol) followed by NaOH (2.5N, 5 mL). Ethyl iodide (3.9 g, 2.0 mL, 25 mmol) was added and the mixture was stirred vigorously for 2 d then worked up as follows. The reaction mixture was diluted with water and DCM. The aqueous layer was separated and extracted once with DCM. The combined organic layers were washed with water, dried over Na2SO4, filtered, and concentrated in vacuo to give an oil. Flash chromatography (SiO2, 1:9 EtOAc:Hexanes to 1:1 EtOAc:Hexanes) to provide 100 mg, 26%, of the title compound as a yellow oil.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted once with DCM
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an oil

Sources & evidence

ORD record
ord-250cc7bea9c743399cee296656daf8e6
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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