3-(4-Hydroxybut-1-ynyl)phenyl acetate → HCID 68981033, compound
Reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[C:12][CH2:13][CH2:14][OH:15])[CH:6]=1)(=[O:3])[CH3:2]>C(OCC)(=O)C.C(O)C.[Pd]>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=1)(=[O:3])[CH3:2]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 3-(4-hydroxybut-1-ynyl)phenyl acetate (4.47 g) was hydrogenated over 5% Pd on carbon in ethyl acetate (100 mL) and ethanol (100 mL) over 20 h. The reaction mixture was filtered through celite under nitrogen, and the filtrate was concentrated in vacua. The residue was purified by chromatography (SPE, gradient from cyclohexane to EtOAc) to give the title compound. LCMS RT=2.64 min
Workup
- filtrationThe reaction mixture was filtered through celite under nitrogen
- concentrationthe filtrate was concentrated in vacua
- customThe residue was purified by chromatography (SPE, gradient from cyclohexane to EtOAc)
Sources & evidence
- ORD record
- ord-4371f1abf2874ab6b921aeff0b4848f1
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07271197B2
Reaction notes
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