Citric Acid → 1-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]ethanol

HRID 1881871Notes

Reaction equation

HRID 1881871 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([CH:11]=[O:12])=[CH:9][N:10]=1.[C:13](O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[S:7][C:8]([CH:11]([OH:12])[CH3:13])=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 311Citric AcidHCID 593313182-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde

Product 1

HCID 593314621-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]ethanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(1,3-dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde (2.25 g) in tetrahydrofuran (20 mL) was slowly added a 1.13M methyllithium diethyl ether solution (12.0 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 30 min, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (1.96 g, yield 80%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). MS: 202 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e1a5fa507f894b018c62435913b5fc4d
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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