반응 #73227

반응 방정식

sodium bicarbonate

methanol

p-toluenesulfonic acid

Ozone

dimethyl sulfide

2-norbornene

→

product

3-(Dimethoxymethyl)cyclopentanecarbaldehyde

용매

DCM

반응 조건

후처리

1. 1
   workup.ADDITIONwas added The reaction
2. 2
   온도to warm at 20° C.
3. 3
   workup.STIRRINGwas stirred for 90 minutes
4. 4
   workup.STIRRINGthe resulting mixture was stirred at 20° C. for 30 minutes
5. 5
   workup.STIRRINGThe reaction was stirred for 16 hours
6. 6
   기타was reduced by rotary evaporation to ˜50 mL The reaction
7. 7
   추출was extracted with DCM
8. 8
   세척the organic extracts were washed with water and brine
9. 9
   건조dried (MgSO4)
10. 10
    workup.DISTILLATIONThe reaction was distilled at 135° C. (bath temperature) at high pump vacuum

실험 절차

Into a 3-neck round bottom flask 2-norbornene (5.500 g, 0.05841 mol) was dissolved in DCM (198.0 mL,) and methanol (38.5 mL) and was cooled at −78° C. Ozone was passed through the reaction until it turned blue and was stirred at −78° C. for 30 minutes. Then nitrogen was passed through for 20 minutes and p-toluenesulfonic acid (0.95 g, 0.0055 mol) was added The reaction was allowed to warm at 20° C. and was stirred for 90 minutes. Into the reaction was added sodium bicarbonate (1.67 g, 0.0199 mol) and the resulting mixture was stirred at 20° C. for 30 minutes and dimethyl sulfide (9.4 mL, 0.13 mol) was added. The reaction was stirred for 16 hours and was reduced by rotary evaporation to ˜50 mL The reaction was extracted with DCM and the organic extracts were washed with water and brine, dried (MgSO4), and stripped in vacuo. The reaction was distilled at 135° C. (bath temperature) at high pump vacuum to give the product (7.5 g) as a ˜2:1 mixture of diastereomers. 1H NMR (300 MHz, CDCl3): 9.64 & 9.62 (d, 1H), 4.15 & 4.12 (s, 1H), 3.35 & 3.34 (s, 6H), 2.77 m, 1H), 2.34 (m, 1H), 1.35-2.00 (m, 6H).

출처