Potassium Hydroxide → N-(oxiran-2-ylmethyl)aniline

HRID 332101노트

반응식

HRID 332101 반응식
Cl[CH2:2][CH:3]([OH:12])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[K+]>O1CCOCC1.CCOC(C)=O>[O:12]1[CH2:2][CH:3]1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 36402541-Anilino-3-chloropropan-2-ol

생성물 1

HCID 18522547N-(oxiran-2-ylmethyl)aniline수율 95%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of the product of Step 3 (185.7 mg, 1.0 mmol, 1 equiv) in 1,4-dioxane (3.3 mL) was added KOH powder (67.3 mg, 1.2 mmol, 1.2 equiv). The mixture was stirred at room temperature for 24 hours. The mixture was diluted with EtOAc and washed with 1M HCl and brine. The organic layer was dried with MgSO4 and concentrated to give crude product. It was further purified by silica gel chromatography using 20% EtOAc/Hex to afford 141.8 mg colorless oil as product, yield 95.0%. 1H NMR (CDCl3, 400 MHz) δ=2.70 (dd, J=4.9, 2.3 Hz, 1H) 2.87-2.77 (m, 1H) 3.23-3.18 (m, 1H) 3.26 (t, J=4.9 Hz, 1H) 3.59-3.48 (m, 1H) 3.87 (s, 1H) 6.64 (d, J=7.7 Hz, 2H) 6.73 (t, J=7.3 Hz, 1H) 7.18 (dd, J=8.3, 7.5 Hz, 2H).

후처리

  1. washwashed with 1M HCl and brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. concentrationconcentrated
  4. customto give crude product
  5. customIt was further purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-2e531842168d4c9db4d661a34305bb28
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877797B2

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