Methanol → Methyl 6-phenylnicotinate

HRID 1054100노트

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HRID 1054100 반응식
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N(I)[C:17](=[O:18])C1.C([O-])([O-])=O.[K+].[K+].CO.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C>[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([C:11]([O:18][CH3:17])=[O:12])=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

7

반응물 5

HCID 887MethanolHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 27645626-Phenylnicotinaldehyde

생성물 1

HCID 13129505Methyl 6-phenylnicotinate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 43b (350 mg, 1.91 mmol) in acetonitrile (20 mL) were added NIS (1.29 g, 5.73 mmol), K2CO3 (787 mg, 5.73 mmol) and CH3OH (0.39 mL, 9.55 mmol). After stirring the reaction mixture for 15 h aqueous Na2S2O3-solution (1 g Na2S2O3 in 10 mL water) was added. The resultant mixture was extracted with a solution of 50% ether in hexane (4×20 mL). The combined organic phases were washed with brine and solvent was removed under vacuum. The crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (6:1) as eluent. White solid. Yield: 297 mg, 73%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=3.75 (s, 3H), 7.22-7.30 (m, 3H), 7.59 (dd, J=8.5, 0.9 Hz, 1H), 7.82-7.86 (m, 2H), 8.12 (dd, J=8.5, 2.2 Hz, 1H), 9.06 (dd, J=2.2, 0.9 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=52.3, 119.8, 124.2, 127.3, 128.9, 129.9, 137.8, 138.3, 150.9, 160.9, 165.9; (ESI): m/z=214.02 [M+H]+.

후처리

  1. additionwas added
  2. extractionThe resultant mixture was extracted with a solution of 50% ether in hexane (4×20 mL)
  3. washThe combined organic phases were washed with brine and solvent
  4. customwas removed under vacuum
  5. customThe crude product was purified by flash chromatography on silica-gel
  6. additiona mixture of hexane/ethyl acetate (6:1) as eluent

출처 및 근거

ORD 기록
ord-be4162e221d84575b7e27aafdf4bc497
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394290B2

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