反应 #57289

反应方程式

2-methoxyethoxymethyl chloride

5-hydroxy-2-nitrobenzaldehyde

tetrahydrofuran

N,N-diisopropylethylamine

→

2

收率 97.0%

5-(2-methoxy-ethoxymethoxy)-2-nitro-benzaldehyde

收率 97.0%

溶剂

dichloromethane

反应条件

后处理

1. 1
   其他the resulting reaction mixture
2. 2
   workup.STIRRINGstirred for 10 minutes at 0° C.
3. 3
   温度warmed up to room temperature
4. 4
   workup.STIRRINGto stir at room temperature for 18 hours
5. 5
   浓缩The reaction mixture was concentrated under reduced pressure, and 150 mL of ethyl acetate
6. 6
   workup.ADDITIONwere added
7. 7
   过滤The resulting off-white precipitate was filtered off
8. 8
   其他the filtrate was transferred into a separatory funnel
9. 9
   洗涤The organic layer was washed with 75 mL of 1N sodium hydroxide solution, 100 mL water, and 75 mL brine
10. 10
    干燥The organic layer was dried over anhydrous potassium carbonate
11. 11
    过滤filtered
12. 12
    浓缩concentrated

实验过程

A suspension of 5 g (30 mmol) of 5-hydroxy-2-nitrobenzaldehyde (1) in 100 mL of dichloromethane and 10 mL of freshly distilled tetrahydrofuran was cooled to 0° C. To this suspension 6.25 mL (57 mmol) of N,N-diisopropylethylamine was added, and the resulting reaction mixture was stirred for 5 minutes. To this reaction mixture 3.76 mL (33 mmol) of 2-methoxyethoxymethyl chloride was added, stirred for 10 minutes at 0° C., warmed up to room temperature, and allowed to stir at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and 150 mL of ethyl acetate were added. The resulting off-white precipitate was filtered off, and the filtrate was transferred into a separatory funnel. The organic layer was washed with 75 mL of 1N sodium hydroxide solution, 100 mL water, and 75 mL brine. The organic layer was dried over anhydrous potassium carbonate, filtered, and concentrated to give 7.4 g (29 mmol, 97%) of 2 [LC-MS; M+Na 278].

来源