Triethylamine → 2-((Benzyloxy)methyl)-1,3-dioxane

HRID 1645585Notes

Reaction equation

HRID 1645585 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12](O)[CH2:13][CH2:14][OH:15].C(OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>>[CH2:1]([O:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 104421,3-PropanediolHCID 31214Ethyl orthoformateHCID 108989(Phenylmethoxy)acetaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 597923782-((Benzyloxy)methyl)-1,3-dioxaneYield 58%

Procedure

A mixture of benzyloxyacetaldehyde (3.6 g, 24 mmol), 1,3-propanediol (5.2 ml, 72 mmol), triethyl orthoformate (4 ml, 24 mmol), and p-toluenesulfonic acid monohydrate (414 mg, 2.45 mmol) was stirred at room temperature for 17 hours. To the reaction mixture, triethylamine (669 μl, 4.8 mmol) was added, which was concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (2.9 g, yield: 58%) as a light yellow oil.

Workup

  1. concentrationwhich was concentrated
  2. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Sources & evidence

ORD record
ord-37ef2ef301074b42b15ead7bef35d04e
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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