Acetic Acid → 3-(1,3-Thiazol-2-yl)propan-1-ol

HRID 982396Notes

Reaction equation

HRID 982396 reaction equation
C(O)(=O)C.[S:5]1[CH:9]=[CH:8][N:7]=[C:6]1[C:10]#[C:11][CH2:12][OH:13].N(C([O-])=O)=NC([O-])=O.[K+].[K+]>N1C=CC=CC=1>[S:5]1[CH:9]=[CH:8][N:7]=[C:6]1[CH2:10][CH2:11][CH2:12][OH:13]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 6096233Potassium diazene-1,2-dicarboxylateHCID 11571812HCID 11571812, compound

Product 1

HCID 178291513-(1,3-Thiazol-2-yl)propan-1-olYield 58.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Glacial acetic acid (16 ml) was added dropwise during 0.25 h to a stirred solution of 3-(2-thiazolyl)-2-propynol (2.4 g) and dipotassium azodicarboxylate (50 g) in pyridine (200 ml). The mixture was stirred at room temperature for 1 h and additional glacial acetic acid (40 ml) added during 0.5 h. The mixture was stirred at room temperature for 2 days. The solvent was removed by azeotropic distillation with toluene (2×100 ml) and the residue partitioned between (100 ml) and ethyl acetate (100 ml). The aqueous layer was extracted with ethyl acetate (2×50 ml) and the combined extracts dried and evaporated to leave a brown oil. This was purified by FCC eluting with toluene:ethyl acetate:triethylamine (50:50:1) to give the title compound as an orange oil (1.45 g), t.l.c. (toluene:ethyl acetate:triethylamine 50:50:1) Rf 0.15.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 days
  2. customThe solvent was removed by azeotropic distillation with toluene (2×100 ml)
  3. customthe residue partitioned between (100 ml) and ethyl acetate (100 ml)
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
  5. customthe combined extracts dried
  6. customevaporated
  7. customto leave a brown oil
  8. customThis was purified by FCC
  9. washeluting with toluene:ethyl acetate:triethylamine (50:50:1)

Sources & evidence

ORD record
ord-63efabcd5619444e9ad12ecf3263f9b0
Source dataset
uspto-grants-1991_02
Patent number
US04996218

Reaction notes

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