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CID 6327156 → (R)-2-(2,3-dichlorophenyl) propanoic acid

HRID 64242
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 64242
C([C@@H]1COC(=O)N1[C:14](=[O:25])[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[Cl:24])[CH3:16])C1C=CC=CC=1.[Li].[Li+].[O-:28][O-]>C1COCC1.O>[Cl:24][C:18]1[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:17]=1[C@@H:15]([CH3:16])[C:14]([OH:25])=[O:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6327156CID 6327156HCID 90041040HCID 90041040, Verbindung

Produkt 1

HCID 34175473(R)-2-(2,3-dichlorophenyl) propanoic acidAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of compound 20 (160 mg, 0.42 mmol) in THF (5 mL) and water at 0° C., was added a solution of lithium peroxide (prepared by adding 30% hydrogen peroxide (2.9 mL, 2.10 mmol) to lithium hydroxide (17.6 mg, 0.41 mmol) in water (0.679 mL)) dropwise. The mixture was stirred for 0° C. for 1h, quenched with sat.Na2SO3 (1.28 mL), solvent was removed in vacuo. The mixture was diluted with water and aqueous solution was extracted with DCM twice. The aq.layer was acidified with Conc.HCl and extracted with EtOAc twice. Combined organic layers were washed with brine and dried over MgSO4, concentrated. Purified by column chromatography (EtOAc/n-Hexane 40:60) to afforded compound 21 (80 mg, 86.9%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 1.51 (d, J=7.2 Hz, 3H), 4.27 (q, J=6.8 Hz, 1H), 7.16-7.24 (m, 2H), 7.37 (d, J=7.6 Hz, 1H)).

Aufarbeitung

  1. customquenched
  2. customNa2SO3 (1.28 mL), solvent was removed in vacuo
  3. additionThe mixture was diluted with water and aqueous solution
  4. extractionwas extracted with DCM twice
  5. extractionHCl and extracted with EtOAc twice
  6. washCombined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customPurified by column chromatography (EtOAc/n-Hexane 40:60)

Quellen und Nachweise

ORD-Eintrag
ord-19bffd29974447f38674480a3afbc3de
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09447134B2

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