反应 #66347

反应方程式

[(3-Nitro-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-phosphonic acid dimethyl ester

Sodium hydride

4-picolinaldehyde

→

oil

收率 110.0%

4-[2-(3-nitro-phenyl)-2-(tetrahydro-pyran-2-yloxy)-vinyl]-pyridine

收率 110.0%

溶剂

THF

反应条件

后处理

1. 1
   温度the mixture was heated to 60° C.
2. 2
   workup.STIRRINGstirred at this temperature for 2.5 hours
3. 3
   浓缩The reaction mixture was concentrated under reduced pressure
4. 4
   workup.ADDITIONdiluted with water (500 mL)
5. 5
   workup.ADDITIONby adding a saturated solution of NaHCO3
6. 6
   萃取the mixture was extracted with ethyl acetate (4×300 mL)
7. 7
   干燥The organic layer was dried over Na2SO4
8. 8
   浓缩concentrated to dryness

实验过程

[(3-Nitro-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-phosphonic acid dimethyl ester (40.7 g, 0.105 mol) was dissolved in dry THF (1 L) under nitrogen. Sodium hydride (60% suspension in mineral oil)(6.3 g, 0.158 mol, 1.5 eq) was added and the mixture was stirred for 10 minutes at room temperature. Neat 4-picolinaldehyde (10 mL, 0.105 mol, 1 eq) was then added dropwise and the mixture was heated to 60° C. and stirred at this temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure to ⅓ of the original volume and then diluted with water (500 mL). pH was adjusted to 7-8 by adding a saturated solution of NaHCO3 and the mixture was extracted with ethyl acetate (4×300 mL). The organic layer was dried over Na2SO4 and concentrated to dryness. An oil (37.7 g) was obtained, which was used without further purification in the following step.

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