Acetone → 2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol

HRID 1645640Notes

Reaction equation

HRID 1645640 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 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 6409971,2,4-Butanetriol, (2S)-

Product 1

HCID 110518052-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-olYield 73%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To (S)-(−)-1,2,4-butanetriol (30 g, 283 mmol), acetone (200 ml) and p-toluenesulfonic acid monohydrate (1.4 g, 7.36 mmol) were added and the mixture was stirred at room temperature overnight. To the reaction mixture, triethylamine (4 ml) was added and the mixture was concentrated. The residue was purified by silica gel column chromatography (silica gel 350 g, elution solvent: ethyl acetate/heptane=18/82→6/4) to obtain the title compound (30.2 g, yield: 73%) as a colorless oil.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by silica gel column chromatography (silica gel 350 g, elution solvent: ethyl acetate/heptane=18/82→6/4)

Sources & evidence

ORD record
ord-131e4e2cd7b44c8bbba58753d41fe0db
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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