Cyclobutylcarbinol → Methyl 3-(4-chlorophenyl)-2-cyclobutylmethoxypropanoate

HRID 30370

Reaktionsgleichung

Reaktionsgleichung von HRID 30370
[CH3:1][O:2][C:3](=[O:15])[C:4](=[N+]=[N-])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[CH:16]1([CH2:20][OH:21])[CH2:19][CH2:18][CH2:17]1>C1C=CC=CC=1>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([O:21][CH2:20][CH:16]2[CH2:19][CH2:18][CH2:17]2)[C:3]([O:2][CH3:1])=[O:15])=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 78130CyclobutylcarbinolHCID 73879458Methyl 2-diazo-3-(4-chlorophenyl)propanoate

Produkt 1

HCID 22270441Methyl 3-(4-chlorophenyl)-2-cyclobutylmethoxypropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 500 mg (2.23 mmol) of methyl-2-diazo-3-(4-chlorophenyl)propanoate (obtained from Step A) and 1.05 mL (5 eq; 11.1 mmol) of cyclobutanemethanol in 5 mL benzene in a pressure tube was added 10 mg (1 mole %) of Rh2(OAc)4 catalyst. The tube was sealed and heated to 90° C. for 1.5 h. The solvents were evaporated under reduced pressure and the crude material was taken up in CH2Cl2 and purified by flash chromatography via gradient elution using mixtures of hexane and EtOAc (100:1 to 50:1). This provided the title compound as a clear oil. TLC Rf=0.53 (4:1 hexanes:EtOAc). 500 MHz 1H NMR (CDCl3): δ 1.68 (m, 2H); 1.85 (m, 1H); 1.88 (m, 1H); 2.01 (m, 2H); 2.53 (sep, 1H); 2.98 (m, 2H); 3.24 (dd, 1H); 3.58 (dd, 1H); 3.76 (s, 3H); 3.98 (dd, 1H); 7.20 (d, 2H); 7.28 (d, 2H).

Aufarbeitung

  1. customThe tube was sealed
  2. customThe solvents were evaporated under reduced pressure
  3. custompurified by flash chromatography via gradient elution

Quellen und Nachweise

ORD-Eintrag
ord-e39e49b444e34a0e8bb921bb715389dc
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423067B2

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