HCID 86757662, compound → HCID 57062265, compound

HRID 2269357Notes

Reaction equation

HRID 2269357 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[CH2:9][C@H:10]([C@H:16]([OH:20])[CH2:17][CH2:18][CH3:19])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCOC(C)=O.[Pd]>[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@H:16]([OH:20])[CH2:17][CH2:18][CH3:19])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 86757662HCID 86757662, compound

Product 1

HCID 57062265HCID 57062265, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl (2R,3R)-2-[(2E)-3-phenyl-2-propen-1-yl]-3-hydroxyhexanoate (1.76 g, 6.38 mmol) in 30 mL of EtOAc is treated with 200 mg of 10% palladium on carbon. The resulting suspension is repeatedly evacuated and purged with a hydrogen balloon, then stirred under 1 atmosphere pressure of hydrogen gas for 6 h. The catalyst is filtered and the filtrate is concentrated in vacuo to provide ethyl (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxyhexanoate as an oil (1.70 g, 96% yield).

Workup

  1. customThe resulting suspension is repeatedly evacuated
  2. custompurged with a hydrogen balloon
  3. filtrationThe catalyst is filtered
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-b51a13151120417f8a42998d10c12632
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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