HCID 18791128, compound → HCID 70078035, compound

HRID 1005346Notes

Reaction equation

HRID 1005346 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5](O)[C:4]=2[CH:3]=1.[O:17]=[C:18]([CH:25]1[CH2:28][CH:27]([C:29]([O:31][CH2:32][C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:34])=[O:30])[CH2:26]1)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)(=O)C.C(O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]([CH:19]([C:18](=[O:17])[CH:25]3[CH2:28][CH:27]([C:29]([O:31][CH2:32][C:33]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[O:34])=[O:30])[CH2:26]3)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 18791128HCID 18791128, compoundHCID 22600194HCID 22600194, compound

Product 1

HCID 70078035HCID 70078035, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2-Chloro-9-hydroxythioxanthene (0.72 g, 2.89 mmol) was allowed to react with ethyl 3-oxo-3-(3-phenacyloxycarbonylcyclobutyl)propanoate (0.8 g, 2.41 mmol) in acetic acid (4 ml) and ethanol (4 ml) for 4 days and then heated at 60° C. for 4 hours. Worked up following procedure described in Example 6(i) to give a yellow oil. The crude product was purified by chromatography on flash silica eluting with chloroform then chloroform-methanol (99.5:0.5 then 99:1) to give the title compound as an oil.

Workup

  1. customto give a yellow oil
  2. customThe crude product was purified by chromatography on flash silica eluting with chloroform

Sources & evidence

ORD record
ord-dbb9d92473a1487c9378222e635ad3a2
Source dataset
uspto-grants-2000_04
Patent number
US06054448

Reaction notes

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