Dimethyl Carbonate → Methyl 2-(4-bromopyridin-2-yl)acetate

HRID 572934

반응식

HRID 572934 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[Li+].CC([N-]C(C)C)C.[C:17](=O)([O:20]C)[O:18][CH3:19]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:17]([O:18][CH3:19])=[O:20])[CH:3]=1

참가 물질

5

반응물 3

HCID 12021Dimethyl CarbonateHCID 2724682Lithium diisopropylamideHCID 27628354-Bromo-2-methylpyridine

생성물 1

HCID 84071108Methyl 2-(4-bromopyridin-2-yl)acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 4-bromo-2-methylpyridine (1 g, 5.8 mmol) in 15 mL of anhydrous THF was added LDA (9.2 mL, 2M) dropwise at −70, stirred for 30 min dimethyl carbonate (630 mg, 7.0 mmol) was added dropwise to the above solution. After stirring for another 1 h, LC-MS found the reaction finished. It was quenched by Sat. NH4Cl solution and extracted with EtOAc. The organic layer was separated and evaporated under reduced pressure. The crude product was purified by a standard method to give desired product. LC-MS: m/z (M+H) 231.1.

후처리

  1. additionwas added dropwise to the above solution
  2. customIt was quenched by Sat. NH4Cl solution
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by a standard method

출처 및 근거

ORD 기록
ord-a47a24c68cc7420984d4030bc5703904
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029531B2

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