HCID 53700235, compound → HCID 54204352, compound

HRID 1780054Notes

Reaction equation

HRID 1780054 reaction equation
[C:1]([O:4][C@H:5]([CH3:16])[CH2:6][C:7]#[C:8][CH2:9][O:10][CH:11]([O:13][CH2:14][CH3:15])[CH3:12])(=[O:3])[CH3:2].[H][H]>[Ni].C(O)C>[C:1]([O:4][C@H:5]([CH3:16])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH:11]([O:13][CH2:14][CH3:15])[CH3:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 53700235HCID 53700235, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54204352HCID 54204352, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Alternatively, hydrogenation was run using a mixture of Raney nickel (10 g of slurry) and 5-(R)-acetoxy-1-ethoxyethoxy-2-hexyne (40 g, 0.17 mole) in ethanol (100 ml). The mixture was shaken with hydrogen gas (60 psi) on a Parr shaker for 5 hours. After filtration of the catalyst, the filtrate was evaporated under vacuum. Residual oil was dissolved in hexanes (100 ml) and the mixture was filtered to remove suspended particles. Evaporation of the solvent under reduced pressure provided 5-(R)-acetoxy-1-ethoxyethoxyhexane (40 g).

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe filtrate was evaporated under vacuum
  3. dissolutionResidual oil was dissolved in hexanes (100 ml)
  4. filtrationthe mixture was filtered
  5. customto remove
  6. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-6fb5f78d4c9541aaa3cc4417949e228a
Source dataset
uspto-grants-1997_05
Patent number
US05629423

Reaction notes

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