Reaktion #73477

Reaktionsgleichung

sodium sulphate

vinylmagnesium bromide

2-methyl-propane-2-sulfinic acid 8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-ylmethyleneamide

2-Methyl-propane-2-sulfinic acid 8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-ylmethyleneamide

vinylmagnesium bromide

→

( 106 )

Ausbeute 50.7%

2-Methyl-propane-2-sulfinic acid {1-[8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-allyl}-amide

Ausbeute 50.7%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for 20 h at room temperature
2. 2
   TemperaturThe reaction mixture was cooled to 0° C.
3. 3
   FiltrationThe suspension was filtered over celite
4. 4
   Trocknenthe organic layer was dried over magnesium sulphate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane)

Vorschrift

Under argon, 2.00 g (5.44 mmol) of 2-methyl-propane-2-sulfinic acid 8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-ylmethyleneamide (105) were dissolved in 27 mL of absolute tetrahydrofuran. Then, 5.99 mL (5.99 mmol) of vinylmagnesium bromide (1M in tetrahydrofuran) were added dropwise at 0° C. and the reaction mixture was stirred for 17 h at room temperature. Another 3 mL (3.00 mmol) of vinylmagnesium bromide (1M in tetrahydrofuran) were added and the mixture stirred for 20 h at room temperature. The reaction mixture was cooled to 0° C. and 15 mL of saturated aqueous sodium sulphate solution were added. The suspension was filtered over celite, the organic layer was dried over magnesium sulphate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane) to yield 1.09 g of (106). Rt=0.96 min (Method 18). Detected mass: 396.4 (M+H+).

Quelle