반응 #2254192

반응 방정식

water

1,6-hexanediol

potassium tert-butoxide

1-iodopropane

→

6-propyloxy-1-hexanol

수율 25.0%

용매

dichloromethane

반응 조건

후처리

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

실험 절차

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).

출처