Hydrochloric Acid → 5-(1-Hydroxy-2,2-dimethoxy-1-methylethyl)-1,3-thiazole-2-carbaldehyde

HRID 1881883Notes

Reaction equation

HRID 1881883 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:7][C:8]([C:11]([OH:18])([CH3:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14])=[CH:9][N:10]=1.Cl.C(=O)([O-])O.[Na+]>CC(C)=O>[OH:18][C:11]([C:8]1[S:7][C:6]([CH:2]=[O:1])=[N:10][CH:9]=1)([CH3:17])[CH:12]([O:13][CH3:14])[O:15][CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 593316132-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]-1,1-dimethoxypropan-2-ol

Product 1

HCID 593315475-(1-Hydroxy-2,2-dimethoxy-1-methylethyl)-1,3-thiazole-2-carbaldehydeYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]-1,1-dimethoxypropan-2-ol (1.58 g), 1M hydrochloric acid (5 ml) and acetone (15 mL) was stirred overnight at 60° C. 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 (0.94 g, yield 71%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). melting point 98-99° C.

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-692c64a81e4545a890496d866fd52804
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…