HCID 18620175, compound → HCID 18620119, compound

HRID 1862612Notes

Reaction equation

HRID 1862612 reaction equation
[Cl:1][C:2]1[C:3]([CH:17]2[CH2:19][O:18]2)=[CH:4][C:5]([O:15][CH3:16])=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(OCC)(=O)C.[C].[Pd]>[Cl:1][C:2]1[C:3]([CH2:17][CH2:19][OH:18])=[CH:4][C:5]([O:15][CH3:16])=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 1

HCID 18620175HCID 18620175, compound

Product 1

HCID 18620119HCID 18620119, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-(5-chloro-2-methoxy-4-oxiranylphenoxy)acetate (129 mg) in ethyl acetate (2.5 ml) was added 10% palladium carbon (13 mg), and the mixture was stirred for 3 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. Purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1) gave ethyl 2-[5-chloro-4-(2-hydroxyethyl)-2-methoxyphenoxy]acetate (86 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPurification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-0dc544429e6f4496aad80cf70fd8b856
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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