Hydrochloric Acid → 5-(1,2-Dihydroxy-2-methylpropyl)-1,3-thiazole-2-carbaldehyde

HRID 1881891Notes

Reaction equation

HRID 1881891 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:7][C:8]([CH:11]([OH:16])[C:12]([CH3:15])([OH:14])[CH3:13])=[CH:9][N:10]=1.Cl.O.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:16][CH:11]([C:8]1[S:7][C:6]([CH:2]=[O:1])=[N:10][CH:9]=1)[C:12]([OH:14])([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 593314731-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]-2-methylpropane-1,2-diol

Product 1

HCID 593314165-(1,2-Dihydroxy-2-methylpropyl)-1,3-thiazole-2-carbaldehydeYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]-2-methylpropane-1,2-diol (0.33 g), 1M hydrochloric acid (1 mL), water (2 mL) and tetrahydrofuran (6 mL) was stirred at 60° C. for 6 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, 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 (0.21 g, yield 77%) was obtained as a yellow oil from a fraction eluted with ethyl acetate. 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-f18507960e42431299dfe0f78f367f78
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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