반응 #797062

반응 방정식

5-Methoxy-2-nitro-benzaldehyde

1,2-bis-trimethylsilanyloxy-ethane

Methylene chloride

→

product

수율 99.2%

2-(5-Methoxy-2-nitrophenyl)-1,3-dioxolane

수율 99.2%

용매

K2CO3

반응 조건

후처리

1. 1
   온도to warm up to at 23° C. for 1 day
2. 2
   기타to quench
3. 3
   기타the reaction, and organic layer
4. 4
   기타was separated
5. 5
   기타Removal of solvent
6. 6
   기타gave a oily product, which

실험 절차

5-Methoxy-2-nitro-benzaldehyde (30.00 g, 0.1656 mol) and 1,2-bis-trimethylsilanyloxy-ethane (40.6 mL, 0.166 mol) were placed in a 40 mL vial, followed by Methylene chloride (1000 mL, 20 mol). The reaction mixture was then cooled to −78° C., and trimethylsilyl trifluoromethanesulfonate (1 mL, 0.008 mol) was added dropwise under N2. The reaction mixture was allowed to warm up to at 23° C. for 1 day. A solution of saturated K2CO3 (50 mL) was added to quench the reaction, and organic layer was separated. Removal of solvent gave a oily product, which was treated with ether/hexanes to give a pure solid product (37.0 g, 99%). 1H NMR (MeOD) δ: 8.01 (d, J=9.0 Hz, 1H), 7.29 (d, J=2.8 Hz, 1H), 7.05 (dd, J=8.9, 2.9 Hz, 1H), 6.49 (s, 1H), 4.85 (s, 3H), 3.91 (s, 4H). MS (M+1): 226.10.

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