6-(2-Pyrimidinyl)-5-hexyn-1-ol → 6-(Pyrimidin-2-yl)hexan-1-ol

HRID 982378Notes

Reaction equation

HRID 982378 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 1

HCID 198767486-(2-Pyrimidinyl)-5-hexyn-1-ol

Product 1

HCID 198767736-(Pyrimidin-2-yl)hexan-1-olYield 29.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 6-(2-pyrimidinyl)-5-hexynol (3.09 g) in ethanol (100 ml) was added to a pre-hydrogenated suspension of 10% palladium on charcoal (1.05 g) in ethanol (50 ml) and hydrogenated at room temperature and pressure, filtered and evaporated in vacuo. The residual oil was purified by FCC eluting with ether and System C (99:1-85:15) to give the title compound as a pale yellow oil (0.93 g).

Workup

  1. filtrationpressure, filtered
  2. customevaporated in vacuo
  3. customThe residual oil was purified by FCC
  4. washeluting with ether and System C (99:1-85:15)

Sources & evidence

ORD record
ord-5fb41320c6b84a3eb9a37cbc3c192cfe
Source dataset
uspto-grants-1991_02
Patent number
US04996218

Reaction notes

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