Lithium Hydroxide → 4-(2-trimethylsilanyl-ethoxymethyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

HRID 1363268Notes

Reaction equation

HRID 1363268 reaction equation
[CH3:1][Si:2]([CH3:20])([CH3:19])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]2[S:16][CH:17]=[CH:18][C:8]1=2.[Li+].[OH-]>CCO>[CH3:1][Si:2]([CH3:20])([CH3:19])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[S:16][CH:17]=[CH:18][C:8]1=2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59648515methyl 4-(2-trimethylsilanyl-ethoxymethyl)-4H-thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 596485874-(2-trimethylsilanyl-ethoxymethyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Methyl 4-(2-trimethylsilanyl-ethoxymethyl)-4H-thieno[3,2-b]pyrrole-5-carboxylate (2.89 g, 9.27 mmol) was dissolved in 60 mL EtOH. A 2.0 M solution of LiOH (46 mL) was added and the reaction was heated to 75° C. for 30 min. EtOH was removed with a N2 stream. The residue was taken up in 300 mL water and acidified to pH 2 with conc. HCl, which gave a white precipitate. The precipitate was extracted into EtOAc. The solution was dried (Na2SO4), filtered and evaporated in vacuo to give 4-(2-trimethylsilanyl-ethoxymethyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid (2.57 g, 93% yield). 1H NMR (400 MHz, (CD3)2CO) δ ppm −0.08 (s, 9H) 0.77-0.91 (m, 2H) 3.55 (t, 2H) 5.96 (s, 2H) 7.23 (d, J=5.37 Hz, 1H) 7.31 (s, 1H) 7.55 (d, J=5.37 Hz, 1H).

Workup

  1. customEtOH was removed with a N2 stream
  2. customgave a white precipitate
  3. extractionThe precipitate was extracted into EtOAc
  4. dry with materialThe solution was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4720061a7956448db748cfb20a8936db
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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