Reaktion #1755483

Reaktionsgleichung

5,5-difluoro-1-oxaspiro[2.3]hexane

CH2Cl2

potassium 2-methoxy-4-nitrophenolate

→

3,3-difluoro-1-((2-methoxy-4-nitrophenoxy)methyl)cyclo-butanol

Ausbeute 64.5%

Lösungsmittel

EtOAc

MeCN water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 5% Na2CO3
2. 2
   Trocknendried (MgSO4)
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe crude product was recrystallized from ca. 150 mL MTBE

Vorschrift

A mixture of 5,5-difluoro-1-oxaspiro[2.3]hexane+3 eq. CH2Cl2 (22.52 g, 0.06 mol), potassium 2-methoxy-4-nitrophenolate (12.43 g, 0.060 mol) prepared in Part E and NaH2PO4.H2O (7.45 g, 0.054 mol) in 50 mL MeCN-water (85:15) was heated at 130° C. in a steel bomb for 3.5 h. The reaction mixture was diluted with EtOAc, washed with 5% Na2CO3, dried (MgSO4) and concentrated. The crude product was recrystallized from ca. 150 mL MTBE giving 3,3-difluoro-1-((2-methoxy-4-nitrophenoxy)methyl)cyclo-butanol (11.2 g, 0.039 mol, 64.5% yield) as a light yellow solid. An additional 1.2 g of a slightly less pure desired product was obtained upon concentration of the mother liquor to ca. 50 mL. 1H NMR (400 MHz, CDCl3) δ ppm 7.89 (1 H, dd, J=8.94, 2.64 Hz), 7.76 (1 H, d, J=2.77 Hz), 6.95 (1 H, d, S=9.06 Hz), 4.16 (2 H, s), 3.94 (3 H, s), 3.36 (1 H, s), 2.73-2.92 (4 H, m).

Quelle