Ethyl Acetate → HCID 57672459, compound

HRID 2101814Notes

Reaction equation

HRID 2101814 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH:15]=[C:16]([CH3:18])[CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.CCOC(C)=O>[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([CH2:15][CH:16]([CH3:17])[CH3:18])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 57801818HCID 57801818, compound

Product 1

HCID 57672459HCID 57672459, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
23 °C

Procedure

To a stirred solution of (S)-ethyl 3-(4-hydroxyphenyl)-5-methylhex-4-enoate 14.3 (0.223 g, 0.9 mmol) in EtOAc (5 mL, 51 mmol) at 0° C. was added Pd/C (0.10 g, 0.9 mmol). See Example 14—it is possible that 14.3 is the R enantiomer and that 14.2 is the S enantiomer although it is believed that 14.3 is the enantiomer shown. The reaction mixture was placed under an atmosphere of hydrogen and stirred at 23° C. for 2 hours. The reaction mixture was filtered and concentrated in vacuo. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford (R)-ethyl 3-(4-hydroxyphenyl)-5-methylhexanoate 46.1 (0.223 g, 99% yield) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-680cf0372fd44c0da46eb02a6c21aabc
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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