반응 #1183938

반응 방정식

ethyl acetate hexane

Sodium hydride

1-((Methylthio)methylsulfonyl)benzene

(1S)-1,2-bis(bromomethyl)-1-(3,4-Dichlorophenyl)cyclopropane

→

product

수율 33.1%

(1S,5S)-3-Benzenesulfonyl-1-(3,4-dichlorophenyl)-3-methylsulfanyl-bicyclo[3.1.0]hexane

수율 33.1%

용매

dimethylforamide

DMF

반응 조건

후처리

1. 1
   온도maintained for 30 min at 40° C
2. 2
   기타was brought to room temperature
3. 3
   온도maintained for 7 hours
4. 4
   기타The reaction mass was quenched with water
5. 5
   추출The aqueous layer was extracted with diethyl ether (2×250 mL)
6. 6
   건조The combined organic layer was dried over anhydrous sodium sulfate
7. 7
   여과filtered
8. 8
   기타evaporated under reduced pressure
9. 9
   기타to yield 8 g of crude oil that
10. 10
    기타was purified by column chromatography (silica gel, ethyl acetate/hexane (4:96)

실험 절차

1-((Methylthio)methylsulfonyl)benzene (2.95 g, 14.6 mmole) was dissolved in dry dimethylforamide (DMF, 40 mL). Sodium hydride (1.75 g, 36.5 mmol) was added portion wise under nitrogen atmosphere at 0° C. The mass was gradually heated to 40° C. and maintained for 30 min at 40° C. A solution of (1S)-1,2-bis(bromomethyl)-1-(3,4-Dichlorophenyl)cyclopropane (5.65 g, 14.65 mmol) in DMF (10 mL) was added dropwise for 30 minutes at 0° C. The temperature of the reaction mass was brought to room temperature slowly and maintained for 7 hours. The reaction was monitored by TLC (ethyl acetate/hexane (10:90)). The reaction mass was quenched with water. The aqueous layer was extracted with diethyl ether (2×250 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 8 g of crude oil that was purified by column chromatography (silica gel, ethyl acetate/hexane (4:96) to yield 2 g (33%) of product. 1H NMR δ(300 MHz,CDCl3): 1.73 (1H,m), 1.85 (2H,m), 2.04 (3H,s), 2.29 (2H,m), 2.54 (1H,m),2.88 (1H, dd, J=15 Hz), 7.12 (1H,d,J=3 Hz), 7.15 (1H,d,J=3 Hz), 7.25 (1H,m), 7.3 (1H,d,J=9 Hz), 7.55-7.57 (2H,m), 7.91 (2H,m).

출처