Ethyl (2E)-3-{3-chloro-5-(methyloxy)-4-[(phenylmethyl)oxy]phenyl}-2-propenoate → HCID 58629867, compound

HRID 1391787Notes

Reaction equation

HRID 1391787 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:18]=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]=[C:6]([O:16][CH3:17])[C:7]=1[O:8]CC1C=CC=CC=1>CCOC(C)=O.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]=[C:6]([O:16][CH3:17])[C:7]=1[OH:8]

Participants

4

Reactant 1

HCID 58629823Ethyl (2E)-3-{3-chloro-5-(methyloxy)-4-[(phenylmethyl)oxy]phenyl}-2-propenoate

Product 1

HCID 58629867HCID 58629867, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of ethyl (2E)-3-{3-chloro-5-(methyloxy)-4-[(phenylmethyl)oxy]phenyl}-2-propenoate (441 mg, 1.27 mmol) in EtOAc (9 mL) under nitrogen at ambient temperature was added PtO2 (20 wt %, 88 mg) and the mixture stirred under an atmosphere of hydrogen for 18 h. The resulting mixture was then purified by SPE (silica, 5 g cartridge) with a pad of celite on the top, eluting with EtOAc. The filtrate was then reduced and purified further by SPE (silica, 10 g cartridge) eluting with cyclohexane:EtOAc (gradient 20:1 to 3:1) to give the title compound (287 mg).

Workup

  1. customThe resulting mixture was then purified by SPE (silica, 5 g cartridge) with a pad of celite on the top
  2. washeluting with EtOAc
  3. custompurified further by SPE (silica, 10 g cartridge)
  4. washeluting with cyclohexane

Sources & evidence

ORD record
ord-2acefcfd089d4b82a9cd12e6706547e8
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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