Chloroacetonitrile → 5-Butoxy-3-hydroxythiophene-2-carbonitrile

HRID 65587

反応式

HRID 65587 の反応式
C(O[C:4]([CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[S:8])=[O:5])C.C[O-].[K+].Cl[CH2:18][C:19]#[N:20]>CO>[C:19]([C:18]1[S:8][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:6][C:4]=1[OH:5])#[N:20]

参加物

5

反応物 3

HCID 7856ChloroacetonitrileHCID 21317911Ethyl 3-butoxy-3-sulfanylidenepropanoateHCID 23664618Potassium methoxide2 回

生成物 1

HCID 213179005-Butoxy-3-hydroxythiophene-2-carbonitrile収率 41.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
30 °C

実験手順

205 g of O-n-butyl 2-ethoxycarbonylthioacetate were added at 30° C. to a solution of 70 g of potassium methylate in a liter of methanol and the mixture was stirred for 10 minutes at 30° C. 75.5 g of chloroacetonitrile were added all at once to the mixture which was stirred for an hour at 40° C. and then a solution of 70 g of potassium methylate in 300 ml of methanol. The mixture was stirred for 6 hours at room temperature and was evaporated to dryness. The residue was washed with ethyl acetate and ether and was dried. The residue was then dissolved in water and the aqueous solution was acidified with concentrated hydrochloric acid and was vacuum filtered. The recovered precipitate was washed with water, dried and chromatographed over silica gel. Elution with 6-4 cyclohexane-ethyl acetate yielded 81 g of 2-cyano-3-hydroxy-5-n-butoxy-thiophene melting at 107° C.

後処理

  1. stirringwas stirred for an hour at 40° C.
  2. stirringThe mixture was stirred for 6 hours at room temperature
  3. customwas evaporated to dryness
  4. washThe residue was washed with ethyl acetate and ether
  5. customwas dried
  6. dissolutionThe residue was then dissolved in water
  7. filtrationfiltered
  8. washThe recovered precipitate was washed with water
  9. customdried
  10. customchromatographed over silica gel
  11. washElution with 6-4 cyclohexane-ethyl acetate

出典と根拠

ORDレコード
ord-c1e45e078eb043519707870911ab0059
出典データセット
uspto-grants-1978_12
特許番号
US04128562

関連ノート

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