Triethylamine → 2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanol

HRID 31637Notes

Reaction equation

HRID 31637 reaction equation
[OH:1][CH2:2][CH:3]([CH2:6][CH2:7][OH:8])[CH2:4][OH:5].O.[C:10]1(C)[CH:15]=CC(S(O)(=O)=O)=C[CH:11]=1.C(N(CC)CC)C>CC(C)=O>[CH3:11][C:10]1([CH3:15])[O:5][CH2:4][CH:3]([CH2:6][CH2:7][OH:8])[CH2:2][O:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 110406842-(Hydroxymethyl)butane-1,4-diol

Product 1

HCID 118160112-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanolYield 220.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To an acetone (30 ml) solution of the 2-(hydroxymethyl)butane-1,4-diol (3.4 g, 28.3 mmol) obtained in accordance with the method described in J. Med. Chem., 30 (9), 1636-1642 (1987), p-toluenesulfonic acid monohydrate (244 mg, 2.83 mmol) was added at room temperature and the mixture was stirred for 15 hours. To the reaction mixture, triethylamine (394 μl, 2.83 mmol) was added and the mixture was concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (1.0 g, yield: 22%) as a light yellow oil.

Workup

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

Sources & evidence

ORD record
ord-8a9cc5a7542b44dd8e1333a54c5446fa
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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