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

HRID 368341

Reaction equation

HRID 368341 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-d39cbc6f7b16458c8b10be9544f5fc53
Source dataset
uspto-grants-2000_10
Patent number
US06133303

Linked notes

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