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tert-butyl 1H-pyrrole-2-carboxylate → HCID 12992895, compound

HRID 1821926
Notes
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Reaction equation

HRID 1821926 reaction equation
[C:1]([O:5][C:6]([C:8]1[NH:9][CH:10]=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrC[CH:15]([CH2:32]C([O-])=O)[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:20][CH:19]=1>CS(C)=O.[Na+].[Cl-]>[C:1]([O:5][C:6]([C:8]1[N:9]([CH2:32][CH:15]([O:7][C:6](=[O:5])[CH3:8])[CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:23]=2)[CH:10]=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 15458947tert-butyl 1H-pyrrole-2-carboxylateHCID 86606004HCID 86606004, compound

Product 1

HCID 12992895HCID 12992895, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 5234Sodium ChlorideSolvent

Conditions

Temperature
110 °C

Procedure

0.145 g (0.867 mmol) tert-butylpyrrole-2-carboxylate is dissolved in 10 ml absolute DMSO, mixed with 0.107 g (0.952 mmol) potassium-tert-butylate and stirred at 110° C. for 15 minutes. A solution of 0.333 g (0.864 mmol) [1-bromo-3-(4-octylphenoxy)propan-2-yl]acetate in 10 ml absolute DMSO is added drop-wise. Following heating at 110° C. for 30 minutes and subsequent cooling, hydrolysis is carried out in saturated NaCl solution. Four extractions with diethyl ether, combination of organic phases, concentration to half the volume on the rotary evaporator, three wash steps with saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as the crude product a yellow oil which is purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 80:20) and yields the product as a colorless oil.

Workup

  1. temperatureFollowing heating at 110° C. for 30 minutes
  2. customsubsequent cooling, hydrolysis
  3. extractionFour extractions
  4. concentrationwith diethyl ether, combination of organic phases, concentration to half the volume
  5. customon the rotary evaporator, three
  6. washwash steps with saturated NaCl solution
  7. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  8. customleave as the crude product a yellow oil which
  9. customis purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 80:20)

Sources & evidence

ORD record
ord-66dfdef8f4194287986981a1e0525384
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07608633B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes