Hydrochloric Acid → HCID 66926134, compound

HRID 2170825Notes

Reaction equation

HRID 2170825 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[C:10]([C:14]3[C:15](=[O:29])[CH:16]([CH:21](O)[CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH2:17][C:18]=3[O:19]C)[CH:9]=2)=[CH:4][CH:3]=1.Cl>CC(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH3:13])=[C:10]([CH:14]3[C:15](=[O:29])/[C:16](=[CH:21]/[CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)/[CH2:17][C:18]3=[O:19])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66926137HCID 66926137, compound

Product 1

HCID 66926134HCID 66926134, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-5-[hydroxy-(tetrahydro-pyran-4-yl)-methyl]-3-methoxy-cyclopent-2-enone (280 mg, 0.65 mmol) in acetone (2 ml) was added 2N hydrochloric acid (2 ml) and the reaction heated to 120° C. for 60 minutes by microwave irradiation. The crude reaction was diluted with ethyl acetate (25 ml) and washed with saturated aqueous ammonium chloride solution (25 ml), brine (25 ml) and the organic layer dry loaded onto silica and purified by flash chromatography to give 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopentane-1,3-dione (88 mg).

Workup

  1. customThe crude reaction
  2. washwashed with saturated aqueous ammonium chloride solution (25 ml), brine (25 ml)
  3. customthe organic layer dry loaded onto silica
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a66782b766d74b0fa73a53ecaa288013
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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