Triethylamine → Ethyl (2-propyl-1,3-dioxan-2-yl)acetate

HRID 1645539

Reaction equation

HRID 1645539 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:12](O)[CH2:13][CH2:14][OH:15].C(OC)(OC)OC.C(N(CC)CC)C>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:9]([C:2]1([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[O:15][CH2:14][CH2:13][CH2:12][O:1]1)[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9005Trimethyl orthoformateHCID 104421,3-PropanediolHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 59792385Ethyl (2-propyl-1,3-dioxan-2-yl)acetateYield 80.5%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

A mixture of ethyl 3-oxohexanoate (5 g, 31.6 mmol), 1,3-propanediol (3.61 g, 47.4 mmol), trimethyl orthoformate (5.78 ml, 34.8 mmol), and p-toluenesulfonic acid monohydrate (272 mg, 1.58 mmol) was stirred at room temperature for 22 hours. After completion of the reaction, triethylamine (881 μl, 6.32 mmol) was added to the reaction mixture which was then concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (5.5 g, yield: 80.5%) as a light yellow oil.

Workup

  1. additionwas added to the reaction mixture which
  2. concentrationwas then concentrated
  3. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Sources & evidence

ORD record
ord-d7dfc88dd4f2486aa12d1969aa2027c1
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Linked notes

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