HCID 58572769, compound → HCID 58572374, compound

HRID 1920813Notes

Reaction equation

HRID 1920813 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:15]([O:17][CH2:18][C@H:19]2[CH2:21][O:20]2)[CH3:16])=[C:6](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=1>C(O)C.[Rh]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:15]([O:17][CH2:18][C@H:19]2[CH2:21][O:20]2)[CH3:16])=[C:6]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=1

Participants

4

Reactant 1

HCID 58572769HCID 58572769, compound

Product 1

HCID 58572374HCID 58572374, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl (2E)-3-(5-chloro-2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)acrylate (822 mg, 2.65 mmol), which had been obtained in Example 3 (3c)-15, was dissolved in ethanol (25 mL), added with rhodium/alumina (246 mg), and stirred for 5 hours at room temperature under hydrogen atmosphere. The reaction solution was filtered using Celite. The solvent was distilled off under reduced pressure to give the title compound as a colorless oily substance (816 mg, yield 99%).

Workup

  1. filtrationThe reaction solution was filtered
  2. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-417c7713630e47d98dc0c38607bd8528
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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