Sulfuric Acid → HCID 117840091, compound

HRID 1477652Notes

Reaction equation

HRID 1477652 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][CH:12]=[CH2:13].S(=O)(=O)(O)O.[OH-:20].[Na+].[C:22](#[N:24])[CH3:23]>C(OCC)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[CH2:13][CH:12]([NH:24][C:22](=[O:20])[CH3:23])[CH2:11][CH2:10][O:7]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 680234-FluorobenzaldehydeHCID 693893-Buten-1-ol

Product 1

HCID 117840091HCID 117840091, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To an acetonitrile solution (4.0 mL) of 4-fluorobenzaldehyde (421 μL, 4.00 mmol) and 3-buten-1-ol (679 μL, 8.00 mmol), sulfuric acid (427 μL) was added and the resultant mixture was stirred at room temperature for 2 hours. After completion of the reaction, ethyl acetate and 1 M sodium hydroxide aqueous solution were added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (382 mg, yield 40%).

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b68f24def10d4a08a7e2f6fb0e3ecf4d
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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