Triphenylphosphine → 6-[2-(1H-1-imidazolyl)ethoxy]-7-methyl-1,2,3,4-tetrahydro-1-naphthalenone

HRID 1386408

반응식

HRID 1386408 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]2.[N:14]1([CH2:19][CH2:20]O)[CH:18]=[CH:17][N:16]=[CH:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOC(C)=O>[N:14]1([CH2:19][CH2:20][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[CH3:12])[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]3)[CH:18]=[CH:17][N:16]=[CH:15]1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 74168N-(2-Hydroxyethyl)imidazoleHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 186264826-Hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-one

생성물 1

HCID 186265056-[2-(1H-1-imidazolyl)ethoxy]-7-methyl-1,2,3,4-tetrahydro-1-naphthalenone수율 32.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

Under N2, a solution of 2.08 g (11.8 mmol) of 6-hydroxy-7-methyl-1,2,3,4-tetrahydro-1-naphthalenone in 25 mL of THF was treated with 1.46 g (13.9 mmol) of 2-(1H-1-imidazolyl)-1-ethanol and 3.1 g (11.8 mmol) of triphenylphosphine. The solution was cooled in ice and treated with a solution of 1.9 mL (11.8 mmol) of diethyl azodicarboxylate in 5 mL of THF. The solution was allowed to stir at room temperature overnight. The mixture was diluted with EtOAc and washed twice with H2O, twice with saturated NaHCO3, then with saturated NaCl. Drying over MgSO4 and removal of the solvent under pressure left the crude product. Chromatography on silica gel, eluting with CHCl3/MeOH (95/5) gave the product which was recrystallized from EtOAc/hexane to give 1.05 g (32.9% yield) of the product as a tan solid, mp 118-120° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 271 (M+H+).

후처리

  1. temperatureThe solution was cooled in ice
  2. washwashed twice with H2O, twice with saturated NaHCO3
  3. dry with materialDrying over MgSO4 and removal of the solvent under pressure
  4. waitleft the crude product
  5. washChromatography on silica gel, eluting with CHCl3/MeOH (95/5)
  6. customgave the product which
  7. customwas recrystallized from EtOAc/hexane

출처 및 근거

ORD 기록
ord-664c59cbb62b48df94741240e6f2dcbb
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265422B1

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