80127-39-5 → HCID 18005336, compound

HRID 1602154Notes

Reaction equation

HRID 1602154 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][C:14](=[O:16])[CH:13]=[CH:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.C(N(CC)CC)C.[Pd]>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][C:14](=[O:16])[CH2:13][CH2:12][O:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 1094393080127-39-5

Product 1

HCID 18005336HCID 18005336, compoundYield 56.8%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (RS)-2-benzyloxymethyl-2,3-dihydro-4H-pyran-4-one (0.82 g, J. Org. Chem., 44,811 (1979)) in ethanol (15 ml) containing 10% Pd-C (0.089 g) and triethylamine (10 drops) was hydrogenated until NMR spectroscopy indicated almost complete reaction. The solution was evaporated and the residue purified by silica-gel MPLC [25% EtOAc/hexanes] and then bulb-to-bulb distillation [220° C./2 mmHg] to give the title ketone (0.47 g, 56%).

Workup

  1. customreaction
  2. customThe solution was evaporated
  3. customthe residue purified by silica-gel MPLC [25% EtOAc/hexanes]
  4. distillationbulb-to-bulb distillation [220° C./2 mmHg]

Sources & evidence

ORD record
ord-d3db2e83ce9a4bf0a0f6ade3c88e9c6a
Source dataset
uspto-grants-1999_11
Patent number
US05981528

Reaction notes

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