تفاعل #57289

معادلة التفاعل

2-methoxyethoxymethyl chloride

5-hydroxy-2-nitrobenzaldehyde

tetrahydrofuran

N,N-diisopropylethylamine

→

2

المردود 97.0%

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

المردود 97.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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].

المصدر