Iodoethane → N-{3-ethoxybicyclo[1.1.1]pentan-1-yl}acetamide

HRID 62607

반응식

HRID 62607 반응식
[OH:1][C:2]12[CH2:6][C:4]([NH:7][C:8](=[O:10])[CH3:9])([CH2:5]1)[CH2:3]2.[H-].[Na+].I[CH2:14][CH3:15]>C1COCC1>[CH2:14]([O:1][C:2]12[CH2:6][C:4]([NH:7][C:8](=[O:10])[CH3:9])([CH2:5]1)[CH2:3]2)[CH3:15]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 86287953N-{3-hydroxybicyclo[1.1.1]pentan-1-yl}acetamide

생성물 1

HCID 86287954N-{3-ethoxybicyclo[1.1.1]pentan-1-yl}acetamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a anhydrous THF (5 mL) solution of N-(3-hydroxybicyclo[1.1.1]pentan-1-yl)acetamide (1) (1 mmol) is added NaH (60% dispersion in mineral oil, 3 mmol) portionwise at 0° C. After addition, the mixture is stirred until the evolution of gas stops. Iodoethane (1 mmol) is then added by syringe slowly. The reaction is monitored by LCMS and TLC. After consumption of starting material, the reaction mixture is quenched by adding water (3 mL) and extracted with ethyl acetate (3×). The organic layers are combined, dried (magnesium sulfate), filtered, and concentrated. The crude residue is subjected to flash chromatography (silica gel, EtOAc/hexanes) to afford N-(3-ethoxybicyclo[1.1.1]pentan-1-yl)acetamide (2).

후처리

  1. additionAfter addition
  2. customAfter consumption of starting material
  3. customthe reaction mixture is quenched
  4. additionby adding water (3 mL)
  5. extractionextracted with ethyl acetate (3×)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7041294fee3745909557675e4ea95d88
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447025B2

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