Diethyl Carbonate → Ethyl 2-(4-broMopyridin-2-yl)acetate

HRID 1528600노트

반응식

HRID 1528600 반응식
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH3:16])[CH:11]=1.[C:17](=O)([O:21]CC)[O:18][CH2:19][CH3:20]>O1CCCC1>[CH2:19]([O:18][C:17](=[O:21])[CH2:16][C:12]1[CH:11]=[C:10]([Br:9])[CH:15]=[CH:14][N:13]=1)[CH3:20]

참가 물질

5

반응물 3

HCID 7766Diethyl CarbonateHCID 2724682Lithium diisopropylamide2회HCID 27628354-Bromo-2-methylpyridine

생성물 1

HCID 53419398Ethyl 2-(4-broMopyridin-2-yl)acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

Lithium diisopropylamide (2 mol/L in tetrahydrofuran/heptane/ethylbenzene, 3.00 mL) was added to a solution of 4-bromo-2-methylpyridine (2.00 g) and diethyl carbonate (1.8 mL) in tetrahydrofuran (30 mL) cooled to −70° C. The solution was stirred for 1 h prior to the addition of another portion of lithium diisopropylamide (2 mol/L in tetrahydrofuran/heptane/ethylbenzene, 3.00 mL). Stirring was continued at −70° C. for one more hour and then the reaction was quenched by the addition of water. The resulting mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→1:1) to give the title compound. Yield: 2.35 g (83% of theory); LC (method 3): tR=2.86 min; Mass spectrum (ESI+): m/z=244/246 (Br) [M+H]+.

후처리

  1. stirringStirring
  2. customwas continued at −70° C. for one more hour
  3. customthe reaction was quenched by the addition of water
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe combined extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated
  8. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→1:1)

출처 및 근거

ORD 기록
ord-1c34bf2c51354f6f8072399987444e41
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090605B2

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