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Methyl chloroformate → Methyl 2,3-dihydro-1H-indole-1-carboxylate

HRID 965544
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 965544
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:11]([O:13][CH3:14])=[O:12]>N1C=CC=CC=1.C(Cl)Cl>[CH3:14][O:13][C:11]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)=[O:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6586Methyl chloroformate2×HCID 10328Indoline

Produkt 1

HCID 690083Methyl 2,3-dihydro-1H-indole-1-carboxylateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 10 g of indoline in 10 ml of pyridine is cooled to 0° C. a solution of 7.9 g of methyl chloroformate in 10 ml of DCM is added dropwise and the mixture is stirred for 1 hour at 0C. A further solution of 7.9 g of methyl chloroformate in 10 ml of DCM is then added and the reaction mixture is concentrated under vacuum. The residue is taken up with water and extracted with AcOEt, the organic phase is washed with a 5% solution of potassium hydrogensulfate, with water and with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum to give 8.3 g of the expected product after trituration in a DCM/iso ether mixture and then filtration. M.p.=69°-70° C.

Aufarbeitung

  1. additionis added dropwise
  2. concentrationthe reaction mixture is concentrated under vacuum
  3. extractionextracted with AcOEt
  4. washthe organic phase is washed with a 5% solution of potassium hydrogensulfate, with water and with a saturated solution of NaCl
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated off under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c127e19238534cd3b50943ffc8b677e8
Quelldatensatz
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05773612

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