반응 #57289

반응 방정식

2-methoxyethoxymethyl chloride

5-hydroxy-2-nitrobenzaldehyde

tetrahydrofuran

N,N-diisopropylethylamine

→

2

수율 97.0%

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

수율 97.0%

용매

dichloromethane

반응 조건

후처리

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

실험 절차

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].

출처