Hydrochloric Acid → HCID 66926152, compound

HRID 2170828Notes

Reaction equation

HRID 2170828 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:27])[CH:16]([CH2:21][CH:22]4[CH2:26][CH2:25][O: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:27])[CH:16]([CH2:21][CH:22]4[CH2:26][CH2:25][O: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 66926079HCID 66926079, compound

Product 1

HCID 66926152HCID 66926152, compoundYield 10.4%

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]-3-methoxy-5-(tetrahydro-furan-3-ylmethyl)-cyclopent-2-enone (150 mg, 0.37 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). The solvent was removed under reduce pressure and the residue purified by mass-directed preparative HPLC to give 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-4-(tetrahydro-furan-3-ylmethyl)-cyclopentane-1,3-dione (15 mg).

Workup

  1. customThe crude reaction
  2. washwashed with saturated aqueous ammonium chloride solution (25 ml), brine (25 ml)
  3. customThe solvent was removed
  4. customthe residue purified by mass-directed preparative HPLC

Sources & evidence

ORD record
ord-c98f840ecda54bb9a35231aa923ed636
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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