HCID 90282055, compound → HCID 90281984, compound

HRID 1497554Notes

Reaction equation

HRID 1497554 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[CH:4][C:3]=1[C:17]([CH3:24])=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>O1CCCC1.[C].[Rh]>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[CH:5]=[CH:4][C:3]=1[CH:17]([CH3:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 1

HCID 90282055HCID 90282055, compound

Product 1

HCID 90281984HCID 90281984, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 178503043HCID 178503043, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(2-chloro-4-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)buta-2-enoate (525 mg) in tetrahydrofuran (10.0 mL) was added 5% rhodium carbon (200 mg), followed by stirring at room temperature for 18 hours under hydrogen atmosphere. The reaction suspension was filtered through Celite, the filtrate was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain ethyl 3-(2-chloro-4-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)butanoate (282 mg).

Workup

  1. filtrationThe reaction suspension was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-14dba6987cdd474a91bae774226c6495
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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