Triphenylphosphine → HCID 71292840, compound

HRID 1404203Notes

Reaction equation

HRID 1404203 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH:14]([C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1)[CH2:15][CH2:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[OH:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:24][O:23][C:21]1[CH:22]=[C:17]2[C:18](=[CH:19][CH:20]=1)[O:25][CH:14]([C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1)[CH2:15][CH2:16]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 71292823HCID 71292823, compound

Product 1

HCID 71292840HCID 71292840, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Diethyl azodicarboxylate (0.87 ml, 5.53 mmol) was added dropwise at room temperature to a mixture of 2-(3-hydroxy-3-pyrazin-2-yl-propyl)-4-methoxy-phenol (960 mg, 3.69 mmol) and triphenylphosphine (1.45 g, 5.53 mmol) in 20 ml of tetrahydrofuran. After stirring at 20° C. for 1 h, the reaction mixture was concentrated and purified by chromatography on silica gel (ethyl acetate in cyclohexane). 2-(6-Methoxy-chroman-2-yl)-pyrazine was obtained as white crystals (665 mg, 74%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by chromatography on silica gel (ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-879e5fda40874dc697cecf4e2c7b6bdd
Source dataset
uspto-grants-2014_12
Patent number
US08912224B2

Reaction notes

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