Triphenylphosphine → 4-(Cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxybenzonitrile

HRID 706499Notes

Reaction equation

HRID 706499 reaction equation
[CH:1]1([CH:4]([C:6]2[CH:7]=[N:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=2)[OH:5])[CH2:3][CH2:2]1.O[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[O:23][CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:1]1([CH:4]([C:6]2[CH:7]=[N:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=2)[O:5][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=2[O:23][CH3:24])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 781354-Hydroxy-3-methoxybenzonitrileHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 114937957Cyclopropyl(6-methoxypyridin-3-yl)methanol

Product 1

HCID 1181139614-(Cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxybenzonitrileYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred 0° C. solution of cyclopropyl(6-methoxypyridin-3-yl)methanol (3.80 g, 21.20 mmol), 4-hydroxy-3-methoxybenzonitrile (1.60 g, 10.73 mmol), and triphenylphosphine (5.60 g, 21.35 mmol) in tetrahydrofuran (10 mL) was added diethyl azodicarboxylate (3.70 g, 21.25 mmol) dropwise. The resulting mixture was allowed to warm to room temperature. After 2 h, the mixture was concentrated. Chromatographic purification of the residue (silica gel, 10% ethyl acetate in petroleum ether elute) afforded 2.70 g (80%) of 4-(cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxybenzonitrile as a light yellow oil.

Workup

  1. concentrationthe mixture was concentrated
  2. customChromatographic purification of the residue (silica gel, 10% ethyl acetate in petroleum ether elute)

Sources & evidence

ORD record
ord-bd27ef3325434cb3b730a099c5f80de2
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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