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

HRID 572934

反応式

HRID 572934 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a47a24c68cc7420984d4030bc5703904
出典データセット
uspto-grants-2015_05
特許番号
US09029531B2

関連ノート

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