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

HRID 2178380Notes

Reaction equation

HRID 2178380 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-ac750ee058994c06b94fa55a67f31ba8
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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