Ethanol → N-(6-fluoro-2-naphthyl)carbamic acid ethyl ester

HRID 1270767

반응식

HRID 1270767 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](C(O)=O)[CH:6]=[CH:5]2.C([N:17]([CH2:20]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])=CC=1.[CH2:39]([OH:41])[CH3:40]>O1CCOCC1>[CH2:39]([O:41][C:20](=[O:29])[NH:17][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[CH:8]=1)[CH3:40]

참가 물질

6

반응물 4

HCID 702EthanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27827886-Fluoro-2-naphthoic acid

생성물 1

HCID 68804469N-(6-fluoro-2-naphthyl)carbamic acid ethyl ester

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a suspension of 6-fluoro-2-naphthoic acid (450 mg, 2.37 mmol) and triethylamine (0.66 mL, 4.73 mmol) in 1,4-dioxane (30 mL) at room temperature, is added DPPA (0.77 mL, 3.55 mmol). After stirring at room temperature for 2.5 hours, ethanol (1.38 mL, 23.7 mmol) is added and the reaction is heated to reflux temperature for 12 hours. After cooling to room temperature, the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator to give an oil. Flash chromatography on silica gel (3:1 hexanes/EtOAc) gives N-(6-fluoro-2-naphthyl)carbamic acid ethyl ester as an oil.

후처리

  1. temperaturethe reaction is heated
  2. temperatureto reflux temperature for 12 hours
  3. temperatureAfter cooling to room temperature
  4. customthe mixture is partitioned between EtOAc and water
  5. washThe organic layer is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by rotary evaporator
  8. customto give an oil

출처 및 근거

ORD 기록
ord-9889c43ee7a0494f9237e9f5a932a7c9
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202364B2

연결된 노트

불러오는 중…