Potassium Carbonate → 2-Bromo-3-[oxiranylmethoxy]pyridine

HRID 1611408노트

반응식

HRID 1611408 반응식
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(O[CH2:19][C@H:20]1[O:22][CH2:21]1)(=O)=O>CN(C)C=O>[Br:1][C:2]1[C:7]([O:8][CH2:19][CH:20]2[CH2:21][O:22]2)=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 230702-Bromo-3-pyridinolHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-

생성물 1

HCID 222566772-Bromo-3-[oxiranylmethoxy]pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 25.2 g (0.145 mole) of 2-bromo-3-pyridinol and 30 g (0.22 mole) of potassium carbonate in 80 mL of N,N-dimethylformamide was added 30 g (0.13 mole) of (S)-glycidyl tosylate. The mixture was heated under nitrogen at 55–60° C. for 15 hours. The solvent was then removed in vacuum and replaced with 500 mL of methylene chloride, and the solution was washed with 500 mL of water and with saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was column chromatographed on silica gel with methylene chloride as eluant to give 17 g of the (S)-enantiomer of the title compound as a white solid. 1H-NMR (CDCl3): multiplet 8.01 δ (1H); multiplet 7.22 δ (2H); doublet of doublets 4.38 δ (1H); multiplet 4.04 δ (1H); multiplet 3.40 δ (1H); multiplet 2.95 δ (1H); multiplet 2.85 δ (1H).

후처리

  1. temperatureThe mixture was heated under nitrogen at 55–60° C. for 15 hours
  2. customThe solvent was then removed in vacuum
  3. washthe solution was washed with 500 mL of water and with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customchromatographed on silica gel with methylene chloride as eluant

출처 및 근거

ORD 기록
ord-4966b52163534dedb060a460e7008fc1
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06987117B2

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