Phenyl chloroformate → Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)phenylcarbamate

HRID 1842972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842972
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH2:11][OH:12])[CH2:9][OH:10])=[CH:4][CH:3]=1.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16]>C([O-])(O)=O.[Na+].O.C1COCC1>[OH:10][CH2:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:15](=[O:16])[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)([CH3:13])[CH2:11][OH:12]

Komponenten

6

Edukt 2

HCID 15891Phenyl chloroformateHCID 594100922-(4-Aminophenyl)-2-methylpropane-1,3-diol

Produkt 1

HCID 86672164Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)phenylcarbamateAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 2-(4-aminophenyl)-2-methylpropane-1,3-diol (1 g, 5.52 mmol, 1.0 eq) in sat. aq. NaHCO3 (4 mL), water (2 mL) and THF (4 mL) was added phenyl chloroformate (0.76 mL, 6.08 mmol, 1.1 eq) at 0° C. and the mixture was stirred at 0° C. for 0.5 h. The mixture was diluted with water (10 mL) and extracted with EtOAc (2×30 mL). The combined organic layer was washed with brine (10 mL) and the solvent evaporated. The crude product was purified by CC using chloroform/MeOH (95:5) as eluent to get phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)phenylcarbamate (1.1 g, 60%) as a white solid (TLC system: chloroform—MeOH; 9:1; Rf: 0.4).

Aufarbeitung

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic layer was washed with brine (10 mL)
  3. customthe solvent evaporated
  4. customThe crude product was purified by CC

Quellen und Nachweise

ORD-Eintrag
ord-a065c8adcd224eadbafb55228de82054
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

Notizen zur Reaktion

Wird geladen…