3-Oxo-3-(2-phenyl-1,3-dioxan-5-yloxy)propyl 2-propylpentanoate → 3-(1,3-Dihydroxypropan-2-yloxy)-3-oxopropyl 2-propylpentanoate

HRID 41816Notes

Reaction equation

HRID 41816 reaction equation
[CH2:1]([CH:4]([CH2:25][CH2:26][CH3:27])[C:5]([O:7][CH2:8][CH2:9][C:10](=[O:24])[O:11][CH:12]1[CH2:17][O:16]C(C2C=CC=CC=2)[O:14][CH2:13]1)=[O:6])[CH2:2][CH3:3]>C(O)C.[Pd]>[CH2:25]([CH:4]([CH2:1][CH2:2][CH3:3])[C:5]([O:7][CH2:8][CH2:9][C:10]([O:11][CH:12]([CH2:13][OH:14])[CH2:17][OH:16])=[O:24])=[O:6])[CH2:26][CH3:27]

Participants

4

Reactant 1

HCID 584552943-Oxo-3-(2-phenyl-1,3-dioxan-5-yloxy)propyl 2-propylpentanoate

Product 1

HCID 584552603-(1,3-Dihydroxypropan-2-yloxy)-3-oxopropyl 2-propylpentanoateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-oxo-3-(2-phenyl-1,3-dioxan-5-yloxy)propyl 2-propylpentanoate (2.99 g, 7.9 mmol) was dissolved in ethanol (90 ml) under argon. Palladium catalyst (10 wt % Pd/C) (300 mg) was added, the flask was evacuated and allowed to stir 1 atm of hydrogen gas at room temperature for 16 hours. The crude reaction mixture was passed through a glass microfiber on a sintered funnel. The volatiles were removed under reduced pressure yielding 2.01 g (6.95 mmol, 88%) of a clear oil. The product was used without any further purification

Workup

  1. customthe flask was evacuated
  2. customThe crude reaction mixture
  3. customwas passed through a glass microfiber on a sintered funnel
  4. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-5725167eda964085a30c99e424e72d17
Source dataset
uspto-grants-2013_09
Patent number
US08535655B2

Reaction notes

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