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

HRID 982396ノート

反応式

HRID 982396 の反応式
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]

参加物

5

反応物 3

HCID 176Acetic Acid2 回HCID 6096233Potassium diazene-1,2-dicarboxylateHCID 115718123-(2-Thiazolyl)-2-propynol

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-63efabcd5619444e9ad12ecf3263f9b0
出典データセット
uspto-grants-1991_02
特許番号
US04996218

反応ノート

読み込み中…