tert-BUTYL CHLORIDE → methyl 5-tert-butyl-1H-pyrrole-2-carboxylate

HRID 635242

Reaktionsgleichung

Reaktionsgleichung von HRID 635242
[Cl-].[Al+3].[Cl-].[Cl-].[NH:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10]([O:12][CH3:13])=[O:11].Cl[C:15]([CH3:18])([CH3:17])[CH3:16]>ClC(Cl)C>[C:15]([C:9]1[NH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=1)([CH3:18])([CH3:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 10486tert-BUTYL CHLORIDEHCID 136930Methyl pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 18322360methyl 5-tert-butyl-1H-pyrrole-2-carboxylateAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Aluminum chloride (0.710 g, 5.33 mmol, 2.2 equiv) is added in one portion to a solution of methyl pyrrole-2-carboxylate (0.30 g, 2.42 mmol) in dry dichloroethane (12 mL) under N2 at rt. Subsequently, 2-chloro-2-methylpropane (0.26 mL, 2.42 mmol, 1.0 equiv) is added in one portion via syringe. After 2 h, the orange solution is quenched by slowly pouring into a saturated sodium bicarbonate solution. The resulting white suspension is extracted with diethyl ether (2×). The combined organic layers are dried (Na2SO4) and concentrated in vacuo to give 0.40 g of methyl 5-t-butylpyrrole-2-carboxylate as an off-white solid. Flash chromatography (40% hexane in dichloromethane) gives 0.3 6 g of the desired material as a white amorphous solid (81%). 1H NMR (CDCl3) d 8.82 (br s, 1H), 6.81 (t, 1H, J=3.3 Hz), 6.00 (t, 1H, J=3.3 Hz), 3.83 (s, 3H), 1.31 (s, 9H).

Aufarbeitung

  1. customthe orange solution is quenched
  2. additionby slowly pouring into a saturated sodium bicarbonate solution
  3. extractionThe resulting white suspension is extracted with diethyl ether (2×)
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e18c61e42f1649dea09eb37e076c2f0d
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187799B1

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