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Sodium Acetate → Ethyl 2-(3-phenylpyrrol-1-yl)acetate

HRID 880463
Notes
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Reaction equation

HRID 880463 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C([O-])(=O)C.[Na+].CO[CH:16]1[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH:18](OC)O1>O.C(O)(=O)C>[C:21]1([C:20]2[CH:19]=[CH:18][N:7]([CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])[CH:16]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 185488262,5-Dimethoxy-3-phenyltetrahydrofuran

Product 1

HCID 66914862Ethyl 2-(3-phenylpyrrol-1-yl)acetateYield 83.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×
HCID 962
Water
Solvent
2×

Conditions

Temperature
80 °C

Procedure

Glycine ethyl ester hydrochloride (0.44 g, 3.17 mmol), sodium acetate (0.47 g, 5.76 mmol) were dissolved in minimum amount of water (5 mL) and added to glacial acetic acid (5 mL). The mixture was heated to 80° C. and then added to a solution of 2,5-dimethoxy-3-phenyl-tetrahydrofuran (0.6 g, 2.88 mmol) in glacial acetic acid (5 mL). The reaction was stirred at 80° C. for 2 h and then diluted with water and extracted with ethyl acetate. The combined organic layers were washed with copious amount of water, dried over anhydrous sodium sulfate and concentrated in vacuo to afford ethyl 2-(3-phenylpyrrol-1-yl)acetate (0.55 g, 83%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with copious amount of water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71cef63c537448f2a1bdedddbfaa17fa
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993574B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes