反応 #337894

反応方程式

3-(4-Chloro-2-fluoro-benzyloxy)-2-hydroxy-benzaldehyde

2-fluoro-ethanol

triphenylphosphine

diisopropyl azodicarboxylate

→

compound

収率 54.0%

3-(4-Chloro-2-fluoro-benzyloxy)-2-(2-fluoro-ethoxy)-benzaldehyde

収率 54.0%

溶媒

water

ethyl acetate

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.WAITat 40° C. for 3 days
2. 2
   その他The organic layers were collected
3. 3
   洗浄washed with brine
4. 4
   乾燥dried over magnesium sulfate
5. 5
   その他After removal of solvent
6. 6
   その他the residue was purified by silica gel column chromatography
7. 7
   洗浄eluting with ethyl acetate in hexanes

実験手順

To a solution of 3-(4-Chloro-2-fluoro-benzyloxy)-2-hydroxy-benzaldehyde (659, 140 mg, 0.5 mmol, prepared by protocol of Example 43, Steps 1 and 2 of Scheme 71, using 4-chloro-2-fluoro-benzyl bromide in place of 4-chloro-benzyl bromide in Step 1) in tetrahydrofuran (8 mL) was added dropwise a mixture of 2-fluoro-ethanol (64 mg, 1.0 mmol), triphenylphosphine (180 mg, 0.7 mmol), and diisopropyl azodicarboxylate (120 mg, 0.6 mol) in tetrahydrofuran (5 ml) at 0° C. The reaction mixture was stirred at 0° C. for 10 minutes and then at 40° C. for 3 days. The reaction mixture was dissolved in water and ethyl acetate. The organic layers were collected, washed with brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexanes to provide the compound as a white solid (660, 88 mg, 54%). MS (ESI) [M+H+]+=327.12.

出典