反応 #6054

反応方程式

1-Benzoyloxy-2-bromomethyl-3-hydroxymethylcyclobutane

tetra-n-butylammonium fluoride

THF

→

title compound

収率 85.0%

1-Benzoyloxy-3-hydroxymethyl-2-methylenecyclobutane

収率 85.0%

溶媒

methylene chloride

反応条件

後処理

1. 1
   洗浄The methylene chloride solution was washed with 150 mL of water
2. 2
   乾燥dried over anhydrous magnesium sulfate
3. 3
   ろ過filtered
4. 4
   濃縮concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue (4.9 g) was dissolved in ~5 mL of methylene chloride
6. 6
   その他purified on a 2.5×35 cm silica gel column
7. 7
   洗浄eluted @ 5 psi with a step-wise (4×200 mL steps) of methanol in methylene chloride from 0% to 3% methanol

実験手順

1-Benzoyloxy-2-bromomethyl-3-hydroxymethylcyclobutane (2.5 g, 8.36 mmol) from Step F and tetra-n-butylammonium fluoride ((8.1 g, 25 mmol) were combined in 200 mL of freshly distilled THF and the reaction mixture was stirred at ambient temperature, under a nitrogen atmosphere, overnight. The volume of the reaction mixture was then reduced to 25 mL and this was dissolved in 250 mL of methylene chloride. The methylene chloride solution was washed with 150 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue (4.9 g) was dissolved in ~5 mL of methylene chloride and purified on a 2.5×35 cm silica gel column eluted @ 5 psi with a step-wise (4×200 mL steps) of methanol in methylene chloride from 0% to 3% methanol to give 1.54 g (85% yield) of the title compound as a syrup; 1H NMR (CDCl3) δ 2.38 (m, 2H), 3.22 (m, 1H), 3.69-3.85 (m, 2H), 5.13 (t, 1H), 5.32 (t, 1H), 5.79 (M, 1H), 7.45 (m, 2H), 7.58 (m, 1H), 8.08 (m, 2H); MS DCI-NH3M/Z: 219 (M+H)+, 236 (M+NH4)+.

出典