Triphenylphosphine → HCID 54451574, compound

HRID 1386389Notes

Reaction equation

HRID 1386389 reaction equation
[C:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][OH:15])[N:10]=[CH:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[CH2:22][CH2:21][CH2:20]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:17]2[CH:26]=[CH:25][C:24]3[C:23](=[O:27])[CH2:22][CH2:21][CH2:20][C:19]=3[CH:18]=2)[N:10]=[CH:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 18626470HCID 18626470, compound

Product 1

HCID 54451574HCID 54451574, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-N-Boc-4-(2-hydroxyethyl)imidazole (1.06 g, 5.0 mmol), 6-hydroxytetralone (0.811 g, 5.0 mmol), and triphenylphosphine (1.44 g, 5.5 mmol) in 10 mL of freshly distilled THF was cooled in an ice bath for 10 minutes and then treated with neat diethyl azodicarboxylate (0.87 mL, 5.5 mmol) added via syringe through a rubber septum. The ice bath was permitted to melt and the reaction continued at room temperature for 5 hours. The solvent was removed in vacuo and the residue was chromatographed (silica gel, 500 g; 1:1, EtOAc:hexanes), and the pure fractions were pooled to afford 0.61 g (33%) of the title compound as a clear, colorless, viscous oil: CI-MS m/e 357 (M++1).

Workup

  1. additionadded via syringe through a rubber septum
  2. customThe solvent was removed in vacuo
  3. customthe residue was chromatographed (silica gel, 500 g; 1:1, EtOAc:hexanes)

Sources & evidence

ORD record
ord-9957bb33130e41bfbec8faf2f716fefe
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

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