3-(4-Hydroxybut-1-ynyl)phenyl acetate → HCID 68981033, compound

HRID 916838Notes

Reaction equation

HRID 916838 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

HCID 693863133-(4-Hydroxybut-1-ynyl)phenyl acetate

Product 1

HCID 68981033HCID 68981033, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

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

  1. filtrationThe reaction mixture was filtered through celite under nitrogen
  2. concentrationthe filtrate was concentrated in vacua
  3. 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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