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

HRID 65587

반응식

HRID 65587 반응식
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]

참가 물질

5

반응물 3

HCID 7856ChloroacetonitrileHCID 21317911Ethyl 3-butoxy-3-sulfanylidenepropanoateHCID 23664618Potassium methoxide2회

생성물 1

HCID 213179005-Butoxy-3-hydroxythiophene-2-carbonitrile수율 41.1%

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
30 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c1e45e078eb043519707870911ab0059
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04128562

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