Hydrochloric Acid → 1-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]ethane-1,2-diol

HRID 1881823Notes

Reaction equation

HRID 1881823 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([C:11](=[O:17])[C:12](OCC)=[O:13])=[CH:9][N:10]=1.[BH4-].[Na+].Cl>C(O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[S:7][C:8]([CH:11]([OH:17])[CH2:12][OH:13])=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59331559Ethyl [2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl](oxo)acetate

Product 1

HCID 593314951-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]ethane-1,2-diolYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl [2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl](oxo)acetate (2.00 g) in ethanol (20 mL) was slowly added sodium borohydride (0.50 g). The reaction mixture was stirred at room temperature for 1 hr, 6M hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give the title compound (1.50 g, yield 89%) as a colorless oil. MS: 218 (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-ee859a4ebfa44a26ae315381f221b6ff
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…