Hydrochloric Acid → HCID 68827228, compound

HRID 2113224Notes

Reaction equation

HRID 2113224 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[S:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1.Cl>CCOC(C)=O>[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:14]2[C:15](=[O:18])[CH2:16][CH2:17][S:12][CH2:13]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66173Tetrahydrothiopyran-4-oneHCID 680234-Fluorobenzaldehyde

Product 1

HCID 68827228HCID 68827228, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Aqueous KOH (0.3 g in 250 mL water) was added to 4-fluoro-benzaldehyde Compound 12a (4.82 g, 38.9 mmol) and tetrahydro-4H-thiopyran-4-one Compound 1a (4.5 g, 38.8 mmol), and the mixture was heated to about 65° C. for 24 hrs, then cooled to r.t. and stirred for 2 hrs. The mixture was acidified to pH 7 with 1.0N HCl (2 mL) and diluted with EtOAc (200 mL). The organic layer was separated, washed with brine and dried with anhydrous Na2SO4, then filtered and concentrated to provide a crude product, which was purified by silica gel column (eluted with 8% EtOAc in hexane) to give 3-(4-fluoro-benzylidene)-tetrahydro-4H-thiopyran-4-one Compound 12b (4.8 g, 48.5%) as a white solid.

Workup

  1. temperaturecooled to r.t.
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a crude product, which
  8. customwas purified by silica gel column (eluted with 8% EtOAc in hexane)

Sources & evidence

ORD record
ord-3e683c4ab2d04659904b6d8ee2006b5e
Source dataset
uspto-grants-2009_04
Patent number
US07524964B2

Reaction notes

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