Ethyl Acetate → HCID 57672532, compound
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
To a stirred solution of (R)-ethyl 3-(4-hydroxyphenyl)-5-methylhex-4-enoate 14.2 (0.200 g, 0.8 mmol) in EtOAc (5 mL, 51 mmol) at 0° C. was added Pd/C (0.09 g, 0.8 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 14.2 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 resulting product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford (S)-ethyl 3-(4-hydroxyphenyl)-5-methylhexanoate 45.1 (0.200 g, 99% yield) as a colorless oil.
Workup
- filtrationThe reaction mixture was filtered
- concentrationconcentrated in vacuo
- customThe resulting product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-aec6e16ffcfa4720a0b491655e8bdbad
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07572934B2
Reaction notes
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