Реакция #2254192

Уравнение реакции

water

1,6-hexanediol

potassium tert-butoxide

1-iodopropane

→

6-propyloxy-1-hexanol

Выход 25.0%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеa 500-mL, one-necked, round-bottom flask equipped with a magnetic stirrer
2. 2
   workup.STIRRINGstirred overnight
3. 3
   ДругоеThe progress of reaction
4. 4
   workup.ADDITIONwas added to the reaction mixture
5. 5
   Экстракцияextracted with ethyl acetate (2×100 mL)
6. 6
   КонцентрированиеThe combined organic layers were concentrated in vacuo
7. 7
   Другоеto get the crude product
8. 8
   Промывкаwashed with water
9. 9
   Сушкаbrine, dried over sodium sulfate
10. 10
    КонцентрированиеThe organic layer was concentrated in vacuo
11. 11
    Другоеto get the crude product
12. 12
    ДругоеThe crude product was purified by column chromatography
13. 13
    Промывкаto elute the product from the column
14. 14
    workup.ADDITIONAll fractions containing the desired pure product
15. 15
    Концентрированиеconcentrated in vacuo

Методика

a 500-mL, one-necked, round-bottom flask equipped with a magnetic stirrer was charged with 1,6-hexanediol (6.00 g), potassium tert-butoxide (5.413 g) at room temperature. The reaction mixture was stirred for one hour, and then 1-iodopropane (8.63 g) was added. The reaction mixture was heated to 70-80° C. and stirred overnight. The progress of reaction was monitored by TLC (Note 1). After completion of the reaction, water was added to the reaction mixture, and extracted with ethyl acetate (2×100 mL). The combined organic layers were concentrated in vacuo to get the crude product. The crude product was dissolved in dichloromethane and washed with water, and then brine, dried over sodium sulfate. The organic layer was concentrated in vacuo to get the crude product. The crude product was purified by column chromatography using 230-400 mesh silica gel. A solvent gradient of ethyl acetate in hexanes (10-45%) was used to elute the product from the column. All fractions containing the desired pure product were combined and concentrated in vacuo to give pure 6-propyloxy-1-hexanol (lot D-1029-048, 1.9 g, 25%) Completion of the reaction was monitored by thin layer chromatography (TLC); (eluent: 60% ethyl acetate in hexanes).

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