Acetone → (4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

HRID 31694Notes

Reaction equation

HRID 31694 reaction equation
[CH2:1]([OH:7])[C@H:2]([OH:6])[CH2:3][CH2:4][OH:5].[CH3:8][C:9]([CH3:11])=O>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>[CH3:8][C:9]1([CH3:11])[O:6][C@H:2]([CH2:3][CH2:4][OH:5])[CH2:1][O:7]1

Participants

5

Reactant 2

HCID 180AcetoneHCID 69942791,2,4-Butanetriol, (2R)-

Product 1

HCID 11480522(4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolaneYield 72.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of (R)-(+)-1,2,4-butanetriol (30 g, 283 mmol), acetone (200 ml, 2724 mmol) and p-toluenesulfonic acid monohydrate (1.4 g, 7.36 mmol) was stirred at room temperature for 16.5 hours. To the reaction mixture, triethylamine was added and the mixture was concentrated. The crude product was purified by silica gel column chromatography (silica gel, elution solvent: heptane/ethyl acetate=1/0→1/1→1/3 gradient). Desired fractions were concentrated to obtain the title compound (29.9 g, 72.3% yield) as a colorless oil.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe crude product was purified by silica gel column chromatography (silica gel, elution solvent: heptane/ethyl acetate=1/0→1/1→1/3 gradient)
  3. concentrationDesired fractions were concentrated

Sources & evidence

ORD record
ord-0a9143f6d9b94b61a36dfe3557820377
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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