تفاعل #73477

معادلة التفاعل

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 )

المردود 50.7%

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

المردود 50.7%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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+).

المصدر