Sodium Sulfate → Methyl 3-hydroxy-3-(4-methoxyphenyl)cyclobutanecarboxylate

HRID 1508478

Reaktionsgleichung

Reaktionsgleichung von HRID 1508478
C([Mg]Br)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[O:12]=[C:13]1[CH2:16][CH:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14]1.[O-]S([O-])(=O)=O.[Na+].[Na+]>CCOCC>[OH:12][C:13]1([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[CH2:16][CH:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14]1

Komponenten

5

Edukt 3

HCID 24436Sodium SulfateHCID 13992367Methyl 3-oxocyclobutane-1-carboxylateHCID 178418276HCID 178418276, Verbindung

Produkt 1

HCID 66524942Methyl 3-hydroxy-3-(4-methoxyphenyl)cyclobutanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

4-Anisylmagnesium bromide (15.6 mL of 0.5 M solution in THF, 7.80 mmol) was added dropwise over 1 h to a stirred solution of methyl 3-oxocyclobutanecarboxylate (1.00 g, 7.80 mmol) in dry Et2O (71.0 mL) at −78° C. under N2. The reaction mixture was allowed to warm to room temperature and was stirred for 1 h. Satd aq. Na2SO4 was added and the mixture was stirred until a clear solution resulted. This mixture was extracted with Et2O (3×50 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 20% EtOAc in hexanes over 2088 mL, gradient to 40% EtOAc in hexanes over 2448 mL) to afford methyl 3-hydroxy-3-(4-methoxyphenyl)cyclobutanecarboxylate. Rf=0.18 (20% EtOAc/hexanes). LCMS calc.=259.10. found=259.01 (M+Na)+. 1H NMR (500 MHz, CHCl3): δ 3.75 (s, 3H); 3.44-3.37 (m, 2H); 3.32-3.18 (m, 3H).

Aufarbeitung

  1. stirringthe mixture was stirred until a clear solution
  2. customresulted
  3. extractionThis mixture was extracted with Et2O (3×50 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThis was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 20% EtOAc in hexanes over 2088 mL, gradient to 40% EtOAc in hexanes over 2448 mL)

Quellen und Nachweise

ORD-Eintrag
ord-9a8f1897f3e6428495db02977088cf6a
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221834B2

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