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

HRID 2380386Notes

Reaction equation

HRID 2380386 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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 dired 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) 12.60 br s, 2 H; 7.53-6.80 m, 3 H; 3.20 t, 1 H; 2.60 t, 2 H; 1.99 q, 2 H. Ir (KBr, v, cm-1) 2900 w, 1710 s, 1410 w, 1260 w, 925 w, 780 s. El. Anal. Calcd. for C9H10O4S: C, 56.45; H, 5.92; S, 18.83. Found: C, 56.39; H, 5.92; S, 18.67.

Workup

  1. customThe resulting reaction
  2. waitfollowed by overnight
  3. temperaturereflux
  4. extractionfollowed by three ether extractions
  5. customevaporated
  6. customto afford a white solid in 90% which
  7. customwas recrystallized from chloroform-hexane
  8. customto produce colorless needles
  9. customMp, 118°-119° C.
  10. customIr (KBr, v, cm-1) 2900 w, 1710 s, 1410 w, 1260 w, 925 w, 780 s

Sources & evidence

ORD record
ord-fb4160a5ee444367af0d837b41a858a0
Source dataset
uspto-grants-1994_11
Patent number
US05367041

Reaction notes

Loading…