5-(1-Naphthyl)-4-pentyn-1-ol → 5-(Naphth-1-yl)pentanol

HRID 1779378Notes

Reaction equation

HRID 1779378 reaction equation
[C:1]1([C:11]#[C:12][CH2:13][CH2:14][CH2:15][OH:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H][H]>[Pd].C(O)C>[C:1]1([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 199555575-(1-Naphthyl)-4-pentyn-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 103532005-(Naphth-1-yl)pentanolYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.5 grams (0.017 mole) of 5-(naphth-1-yl)-4-pentyn-1-ol and 0.5 gram (catalyst) of 10% palladium on carbon in 30 mL of ethanol was shaken in a Parr hydrogenator until the theoretical amount of hydrogen gas was taken up. The reaction mixture was filtered to remove the catalyst, and the filtrate was concentrated under reduced pressure, yielding 3.4 grams of 5-(naphth-1-yl)pentanol. The NMR spectrum was consistent with the proposed structure.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c055d84c10154142a165740fcb62f5d4
Source dataset
uspto-grants-1997_05
Patent number
US05627189

Reaction notes

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