반응 #73477

반응 방정식

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 )

수율 50.7%

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

수율 50.7%

용매

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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+).

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