2-Chloroethanol → 4-(2-chloroethoxy)-1H-indole

HRID 49989

반응식

HRID 49989 반응식
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[Cl:11][CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CCOCC.CCCCCC.C(OCC)C>[Cl:11][CH2:12][CH2:13][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

참가 물질

8

반응물 4

HCID 342-ChloroethanolHCID 11776TriphenylphosphineHCID 754211H-indol-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

생성물 1

HCID 106317214-(2-chloroethoxy)-1H-indole

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 21584099Diethylether hexane용매

실험 절차

A solution of 4-hydroxyindole (3.99 g, 30 mmol), 2-chloroethanol (6.03 ml, 90 mmol) and triphenylphosphine (23.6 g, 90 mmol) in tetrahydrofuran is treated with diethyl azodicarboxylate (14.1 ml, 90 mmol) under nitrogen at room temperature, stirred for 2 hr at room temperature and concentrated in vacuo to give a residue. Cooled diethyl ether is added to the residue and the solid triphenylphosphine oxide is precipitated and removed by filtration. The filtrate is concentrated and purified by flash chromatography (silica gel, EtOAc/hexane: 1.5/8.5) to give an oil. After trituration with Et2O/hexane (1/10), the title compound is obtained as a white solid, 4.8 g (82%) mp 60° C., identified by NMR and mass spectral analyses.

후처리

  1. concentrationconcentrated in vacuo
  2. customto give a residue
  3. customthe solid triphenylphosphine oxide is precipitated
  4. customremoved by filtration
  5. concentrationThe filtrate is concentrated
  6. custompurified by flash chromatography (silica gel, EtOAc/hexane: 1.5/8.5)
  7. customto give an oil

출처 및 근거

ORD 기록
ord-af2ab9939a1c410482122c231543542d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710069B2

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