反応 #57289

反応方程式

2-methoxyethoxymethyl chloride

5-hydroxy-2-nitrobenzaldehyde

tetrahydrofuran

N,N-diisopropylethylamine

→

2

収率 97.0%

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

収率 97.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他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
   濃縮The reaction mixture was concentrated under reduced pressure, and 150 mL of ethyl acetate
6. 6
   workup.ADDITIONwere added
7. 7
   ろ過The resulting off-white precipitate was filtered off
8. 8
   その他the filtrate was transferred into a separatory funnel
9. 9
   洗浄The organic layer was washed with 75 mL of 1N sodium hydroxide solution, 100 mL water, and 75 mL brine
10. 10
    乾燥The organic layer was dried over anhydrous potassium carbonate
11. 11
    ろ過filtered
12. 12
    濃縮concentrated

実験手順

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].

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