Ethyl Acetate → Tert-butyl N-[2-(2-hydroxyethyl)phenyl]carbamate

HRID 1988345노트

반응식

HRID 1988345 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12](CC(O)=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:25](OCC)(=[O:27])[CH3:26]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[CH2:26][CH2:25][OH:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 10752353Tert-butyl N-[2-(2-hydroxyethyl)phenyl]carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

4-(t-butoxycarbonylamino)-benzeneacetic acid (2.9 g, 11.4 mmoles) is dissolved in 10 ml of anhydrous THF at 0° C. and added to a suspension of LiAlH4 (0.52 g, 13.6 mmoles) in 30 ml of THF. The reaction mixture is agitated at ambient temperature for 1.5 hours. 50 ml of ethyl acetate then 20 ml of 2N soda are added to the medium. The expected product is extracted from the organic phase, which is then washed with 3 times 15 ml of water. The organic phase is dried and the solvent evaporated off under reduced pressure. Then the reaction product is purified on silica gel in a dichloromethane/methanol mixture (95/5). 1.1 g (40%) is thus obtained in the form of a colourless oil.

후처리

  1. extractionThe expected product is extracted from the organic phase, which
  2. washis then washed with 3 times 15 ml of water
  3. customThe organic phase is dried
  4. customthe solvent evaporated off under reduced pressure
  5. customThen the reaction product is purified on silica gel in a dichloromethane/methanol mixture (95/5)
  6. custom1.1 g (40%) is thus obtained in the form of a colourless oil

출처 및 근거

ORD 기록
ord-15658b37579c4aaeb998f5f218be48c6
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553976B2

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