HCID 68851499, compound → HCID 68848636, compound

HRID 1826074Notes

Reaction equation

HRID 1826074 reaction equation
CS[CH:3]([C:14]1[CH:19]=[C:18]([C:20]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:21][CH2:22][CH3:23])[CH:17]=[CH:16][C:15]=1[O:29][CH3:30])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]>[Zn].C(O)(=O)C>[CH3:28][CH2:27][O:26][C:24]([C:20]([C:18]1[CH:17]=[CH:16][C:15]([O:29][CH3:30])=[C:14]([CH2:3][C:4]([O:6][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:5])[CH:19]=1)=[CH:21][CH2:22][CH3:23])=[O:25]

Participants

4

Reactant 1

HCID 68851499HCID 68851499, compound

Product 1

HCID 68848636HCID 68848636, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Benzyl 2-methylthio-2-[5-[1-(2-ethoxycarbonyl)butenyl]-2-methoxyphenyl]acetate (2.14 g, 4.99 mmol) and glacial acetic acid (100 mL) were mixed and zinc powder (13.0 g, 199 mmol) was added under stirring at room temperature. After stirring for 6 hours at room temperature, the insolubles were remove by filtration and the filtrate was concentrated. The residue was dissolved into ethyl acetate (50 mL), washed with water and brine, then dried over anhydrous sodium sulfate and concentrated to afford 1.86 g (97%) of the title compound as a pale yellow oil.

Workup

  1. stirringAfter stirring for 6 hours at room temperature
  2. customthe insolubles were remove by filtration
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved into ethyl acetate (50 mL)
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d16ca2e268b54550bada358d19aeac4a
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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