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

HRID 46147노트

반응식

HRID 46147 반응식
C([N-]C(C)C)(C)C.[Li+].CN(C)P(=O)(N(C)C)N(C)C.[CH3:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]=1.[C:29](=O)([O:32]C)[O:30][CH3:31]>C1COCC1>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([CH2:28][C:29]([O:30][CH3:31])=[O:32])[CH:25]=[CH:24][N:23]=1

참가 물질

6

반응물 4

HCID 12021Dimethyl CarbonateHCID 12679HexamethylphosphoramideHCID 2724682Lithium diisopropylamideHCID 142234722-Methoxy-4-methylpyridine

생성물 1

HCID 58951314Methyl 2-(2-methoxypyridin-4-yl)acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To the solution of lithium diisopropylamide (Aldrich, 2.0M, 122 mL, 244 mmol), THF (90 mL) and hexamethylphosphoric triamide (Aldrich, 16 mL, 89 mmol) at −78° C. under nitrogen was added, in 10 min, a solution of 2-methoxy-4-methylpyridine (10.0 g, 81 mmol) in THF (30 mL). After 30 min, a solution of dimethyl carbonate (Aldrich, 7.5 mL, 90 mmol) in THF (30 mL) was added over 15 min. The stirring was continued for 2 h at −78° C. before the reaction was quenched with MeOH (30 mL). The mixture was filtered through Celite and the cake was washed with EtOAc. The filtrate was concentrated in vacuo, and the crude product was purified by silica gel chromatography. MS: 182 (M+1).

후처리

  1. waitThe stirring was continued for 2 h at −78° C. before the reaction
  2. customwas quenched with MeOH (30 mL)
  3. filtrationThe mixture was filtered through Celite
  4. washthe cake was washed with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-cb16aa0748bf4432aed212e7d2e6432c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541592B2

반응 노트

불러오는 중…