Ethanol → [2-(Thiophen-3-yl)ethyl]propanedioic acid

HRID 1033256

반응식

HRID 1033256 반응식
[OH-:1].[K+].C([C:5]([CH2:16]CC(O)=O)([CH2:9][CH2:10][C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)[C:6]([O-:8])=[O:7])C.C([OH:23])C>O>[C:16]([CH:5]([CH2:9][CH2:10][C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)[C:6]([OH:8])=[O:7])([OH:23])=[O:1]

참가 물질

5

반응물 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 86747833Ethyl-2-Carboxyethyl-4-(3-Thienyl)-Butanoate

생성물 1

HCID 54550536[2-(Thiophen-3-yl)ethyl]propanedioic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a stirred solution of 1.4 g (24.96 mmol) of potassium hydroxide in 7.0 ml of 50% ethanol in water, was added the above diester (765 mg, 2.83 mmol) prepared in Example 6. The resulting reaction was allowed to stir at room temperature for two hr, followed by overnight reflux. The resulting mixture was poured into ice-10% HCl, followed by three ether extractions. The combined organic layer was dried with Na2SO4 and evaporated to afford a white solid in 90% which was recrystallized from chloroform-hexane to produce colorless needles. Mp, 118°-119° C.; nmr (DMSO/d6, δ rel TMS) 12.60br s, 2H; 7.53-6.80m, 3H; 3.20t, 1H; 2.60t, 2H; 1.99q, 2H. Ir (KBr, v, cm-1) 2900w, 1710s, 1410w, 1260w, 925w, 780s. El. Anal. Calcd. for C9H10O4S: C, 56.45; H, 5.92; S, 18.83. Found: C, 56.39; H, 5.92; S, 18.67.

후처리

  1. customThe resulting reaction
  2. waitfollowed by overnight
  3. temperaturereflux
  4. extractionfollowed by three ether extractions
  5. dry with materialThe combined organic layer was dried with Na2SO4
  6. customevaporated
  7. customto afford a white solid in 90% which
  8. customwas recrystallized from chloroform-hexane
  9. customto produce colorless needles
  10. customMp, 118°-119° C.

출처 및 근거

ORD 기록
ord-5961026fd5094c069e245569e0ff7f8b
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05310781

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