Water → (Thieno[3,2-b]pyridin-7-yl)acetic Acid Ethyl Ester

HRID 557201Notes

Reaction equation

HRID 557201 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]2[CH:17]=[CH:18][S:19][C:12]=12)C(OCC)=O)[CH3:2].O.[Cl-].[Li+]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:11]1[CH:16]=[CH:15][N:14]=[C:13]2[CH:17]=[CH:18][S:19][C:12]=12)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 673377292-Thieno[3,2-b]pyridin-7-yl-malonic Acid Diethyl Ester

Product 1

HCID 67338527(Thieno[3,2-b]pyridin-7-yl)acetic Acid Ethyl EsterYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

Dissolve 2-(thieno[3,2-b]pyridin-7-yl)malonic acid diethyl ester (12.90 g, 44.0 mmol) in dimethyl sulfoxide (295 mL). Add water (0.79 mL) and lithium chloride (3.73 g, 87.9). Heat the solution to 110° C. for 3 hours. Quench the reaction with saturated brine (3 L) and extract with ethyl acetate (3×1 L). Rewash the organic layers with saturated brine (1 L). Treat the organic layers with magnesium sulfate, filter and concentrate. The residue was purified on silica using 25% ethyl acetate/hexanes to yield the desired compound (5.25 g, 54%).

Workup

  1. customQuench
  2. customthe reaction with saturated brine (3 L)
  3. extractionextract with ethyl acetate (3×1 L)
  4. additionTreat the organic layers with magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customThe residue was purified on silica using 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f6afd0aa03794bae9589c3a549585f6d
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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